Publications by authors named "Xinxin Wu"

52 Publications

Radical-mediated rearrangements: past, present, and future.

Chem Soc Rev 2021 Oct 18;50(20):11577-11613. Epub 2021 Oct 18.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.

Rearrangement reactions, one of the most significant transformations in organic chemistry, play an irreplaceable role in improving synthetic efficiency and molecular complexity. Concomitant cleavage and reconstruction of chemical bonds can display the great artistry and the glamour of synthetic chemistry. Over the past century, ionic rearrangement reactions, in particular those involving cationic pathways, have represented most of the research. Alongside the renaissance of radical chemistry, radical-mediated rearrangements have recently seen a rapid increase of attention from the chemical community. Many new radical rearrangements that extensively reveal the migratory behaviour of functional groups have been unveiled in the last decade. This Review provides a comprehensive perspective on the area from the past to present achievements, and brings up the prospects that may inspire colleagues to develop more useful synthetic tools based on radical rearrangements.
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http://dx.doi.org/10.1039/d1cs00529dDOI Listing
October 2021

Clinical predictive risk factors prolonged the duration of SARS-CoV-2 clearance in 279 moderate COVID-19 patients: A multicenter retrospective cohort study.

Medicine (Baltimore) 2021 Oct;100(40):e27410

LongHua Hospital Shanghai University of Traditional Chinese Medicine, No. 725 Wanping South Road, Xuhui District, Shanghai, China.

Abstract: The results of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) nucleic acid as one of the criteria has been widely applied to assess whether the coronavirus disease 2019 (COVID-19) patients could discharge, however, the risk factors that affect the duration of the SARS-CoV-2 clearance remained to be an enigma. Our research was to identify risk factors correlated with prolonged duration of the SARS-CoV-2 clearance in moderate COVID-19 patients.We retrospectively analyzed 279 consecutive ordinary COVID-19 patients in 3 hospitals in Hubei province including Huangshi Hospital of Infectious Disease, Wuhan Thunder God Mountain Hospital, and Tongji Hospital. Eight clinical characters were contained as risk factors. We used a logistic regression model and nomogram to assess the possibility that the SARS-CoV-2 nucleic acid may turn negative in 14 days.Time from symptoms onset to diagnosis (odds ratio [OR] = 3.18; 95% confidence interval [CI] 1.56-6.46; P = .001), time from onset use of antiviral drugs to onset of symptoms (OR = 0.41; 95% CI 0.23-0.72; P = .02), and bacterial coinfection (OR = 0.07; 95% CI 0.01-0.86; P = .038) were independent risks factors for the duration of SARS-CoV-2 nucleic acid clearance. The regression model showed good accuracy and sensitivity (area under the curve  = 0.96). Nomogram was also provided to predict the negative conversion rate of SARS-CoV-2 nucleic acids within 14 days.Time from symptoms onset to diagnosi, time from onset use of antiviral drugs to onset of symptoms, and bacterial coinfection were independent risk factors for the time of SARS-CoV-2 nucleic acid turning negative in ordinary COVID-19 patients. However, the age, gender, underlying disease, fungal coinfection, and duration use of antiviral drugs were irrelevant factors.
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http://dx.doi.org/10.1097/MD.0000000000027410DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8500613PMC
October 2021

Photocatalytic intermolecular carboarylation of alkenes by selective C-O bond cleavage of diarylethers.

Chem Commun (Camb) 2021 Sep 14;57(73):9240-9243. Epub 2021 Sep 14.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.

Disclosed herein is a novel radical-mediated intermolecular carboarylation of alkenes by cleaving inert C-O bonds. The strategically designed arylbenzothiazolylether diazonium salts are harnessed as dual-function reagents. A vast array of alkenes are proven to be suitable substrates. The benzothiazolyl moiety in the products serves as the formyl precursor, and the OH residue provides the cross-coupling site for further product elaboration, indicating the robust transformability of the products.
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http://dx.doi.org/10.1039/d1cc04038cDOI Listing
September 2021

Application of covered stent graft in the treatment of complex carotid artery lesions: A single center experience.

Vascular 2021 Aug 28:17085381211040991. Epub 2021 Aug 28.

66322LongHua Hospital Shanghai University of Traditional Chinese Medicine, Shanghai, China.

Purpose: To assess the clinical efficiency and imaging outcome of applying covered stent grafts for the treatment of complex carotid artery lesions.

Method: A total of 39 consecutive patients with carotid artery lesions treated with covered stent grafts at our institution from December 2016 to December 2019 were reviewed. Two kinds of stent including self-expandable covered stent (Viabahn; W. L. Gore & Associates) and balloon-expandable covered stent (Willis; Microport) were applied. The angiograms immediately after the procedure, perioperative complications, and follow-up outcomes were recorded.

Result: Based on imaging features, 11 patients exhibited pseudoaneurysms, 23 patients had blood blister-like aneurysms (BBAs), and five patients were carotid cavernous fistulas. A total of 40 stent implantations were performed, including nine Viabahn stents and 31 Willis stents. Two patients received double implants of Willis stents. Stent failed to perform for one patient due to tortuous parent artery. The angiography reports immediately after the procedure showed that the lesions in 36 patients were completely occluded, whereas two patients had minimal endoleaks. With respect to the occurrence of procedural complications, an aneurysm ruptured during the procedure in one case, which resulted in CCF, and acute in-stent thrombosis occurred in another case. Clinical and angiographic follow-up (11.2±2.4 months) sessions were conducted for 38 patients and a complete lesion exclusion was achieved in 36 patients. The minimal endoleak persisted in one patient and another patient experienced recurrence with stent migration, leading to ipsilateral blepharoptosis. However, none of the patients developed hemorrhage or ischemia and in-stent stenosis was not observed.

Conclusion: Covered stent grafts appear to be a safe and feasible for the treatment of complex carotid artery lesions. Despite the potential for stent delivery failure as well as endoleak and procedure-related complications, covered stent grafts should be considered when selecting the optimal treatment strategy.
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http://dx.doi.org/10.1177/17085381211040991DOI Listing
August 2021

Baidu Jieduan granules, traditional Chinese medicine, in the treatment of moderate coronavirus disease-2019 (COVID-19): study protocol for an open-label, randomized controlled clinical trial.

Trials 2021 Jul 22;22(1):476. Epub 2021 Jul 22.

Shanghai University of Traditional Chinese Medicine, 1200 Cai Lun Road, Zhangjiang Hi-Tech Park, Pudong New Area, Shanghai, 201203, China.

Background: Currently, coronavirus disease-2019 (COVID-19) is continuously and rapidly circulating, resulting in serious and extensive effects on human health. Due to the absence of antiviral medicine for COVID-19 thus far, there is a desperate need to develop effective medicine. Traditional Chinese medicine (TCM) has been widely applied in the treatment of epidemic diseases in China, with the aim of achieving clinical efficacy and decreasing the use of antibiotics and glucocorticoids. The aim of this study was to evaluate the efficacy and safety of Baidu Jieduan granules in treating COVID-19.

Methods/design: This multicentre, open-label, randomized controlled trial will be conducted in 300 patients with COVID-19. The patients will be randomly (1:1) divided into a treatment group and a control group. All patients will receive standard therapy at the same time. Patients in the experimental group will receive Baidu Jieduan granule treatment twice a day for 14 days. The outcomes will be assessed at baseline and at 3, 5, 7 and 14 days after treatment initiation. The primary outcome will be the rate of symptom (fever, fatigue and coughing) recovery. Adverse events (AEs) will be monitored throughout the trial.

Discussion: The study will provide high-quality clinical evidence to support the efficacy and safety of Baidu Jieduan granules in the treatment of moderate COVID-19, and enrich the theory and practice of TCM in treating COVID-19.

Trial Registration: Chinese Clinical Trial Registry ChiCTR2000029869 . Registered on 15 February 2020.
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http://dx.doi.org/10.1186/s13063-021-05418-yDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8295640PMC
July 2021

Radiomics Nomogram for Identifying Sub-1 cm Benign and Malignant Thyroid Lesions.

Front Oncol 2021 7;11:580886. Epub 2021 Jun 7.

Department of Otorhinolaryngology-Head and Neck Surgery, Yantai Yuhuangding Hospital, Qingdao University, Yantai, China.

Purpose: To develop and validate a radiomics nomogram for identifying sub-1 cm benign and malignant thyroid lesions.

Method: A total of 171 eligible patients with sub-1 cm thyroid lesions (56 benign and 115 malignant) who were treated in Yantai Yuhuangding Hospital between January and September 2019 were retrospectively collected and randomly divided into training (n = 136) and validation sets (n = 35). The radiomics features were extracted from unenhanced and arterial contrast-enhanced computed tomography images of each patient. In the training set, one-way analysis of variance and least absolute shrinkage and selection operator (LASSO) logistic regression were used to select the features related to benign and malignant lesions, and the LASSO algorithm was used to construct the radiomics signature. Combined with clinical independent predictive factors, a radiomics nomogram was constructed with a multivariate logistic regression model. The performance of the radiomics nomogram was evaluated by using the receiver operating characteristic (ROC) and calibration curves in the training and validation sets. The clinical usefulness was evaluated by using decision curve analysis (DCA).

Results: The radiomics signature consisting of 13 selected features achieved favorable prediction efficiency. The radiomics nomogram, which incorporated radiomics signature and clinical independent predictive factors including age and Thyroid Imaging Reporting and Data System category, showed good calibration and discrimination in the training (area under the ROC [AUC]: 0.853; 95% confidence interval [CI]: 0.797, 0.899) and validation sets (AUC: 0.851; 95% CI: 0.735, 0.931). DCA demonstrated that the nomogram was clinically useful.

Conclusion: As a noninvasive preoperative prediction tool, the radiomics nomogram incorporating radiomics signature and clinical predictive factors shows favorable predictive efficiency for identifying sub-1 cm benign and malignant thyroid lesions.
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http://dx.doi.org/10.3389/fonc.2021.580886DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8215667PMC
June 2021

Alkene Difunctionalization Triggered by a Stabilized Allenyl Radical: Concomitant Installation of Two Unsaturated C-C Bonds.

Angew Chem Int Ed Engl 2021 09 28;60(37):20215-20219. Epub 2021 Jul 28.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.

Radical-mediated difunctionalization of alkenes provides a promising approach to introduce one alkenyl or alkynyl group to target compounds. However, simultaneous installation of two unsaturated C-C bonds via alkene difunctionalization remains elusive, attributable to the high instability and transient lifetimes of alkenyl and alkynyl radicals. Herein, we report the photocatalytic 1,2-alkynylalkenylation and 1,2-enynylalkenylation of alkenes for the first time, triggered by the intermolecular addition of a stabilized allenyl radical to an alkene. A portfolio of strategically designed, easily accessible dual-function reagents are applied to a radical docking-migration cascade. The protocol has broad substrate scope and efficiently increases the degree of unsaturation.
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http://dx.doi.org/10.1002/anie.202106145DOI Listing
September 2021

Nitrogen influenced competition between the genders of  Salix rehderiana.

Tree Physiol 2021 Jun 17. Epub 2021 Jun 17.

Key Laboratory of Bio-Resource and Eco-Environment of Ministry of Education, College of Life Sciences, Sichuan University, Chengdu 610065, China.

Male and female willow plants show spatial segregation of genders along the environmental gradients. Skewed gender ratio of willows is not only related to altitude, but also to nutrient status and sexual competition, which can affect their growth and defense by altering secondary metabolite production. The relationship between metabolites and nutrients in the two genders of Salix rehderiana was explored in the Gongga Mountain. We found gender ratio was altered with a change in soil nitrogen (N) status; in the high N habitats, secondary metabolites accumulated in males. Furthermore, pot experiment was conducted to test the effect of nitrogen supply on gender competition in S. rehderiana. Sufficient N supply stimulated females to produce amino acids and carbon-containing secondary metabolites for maintaining their carbon-nitrogen balance, but extra nitrogen for males was used for growth to occupy more space. N supply induced foliar nutrient imbalances and growth of opportunistic species, allowing them to outcompete neighbors. Better carbon allocation and storage in male than female willows would benefit intersexual competitiveness of males if environment N increases. Competition between the genders has a significant correlation with skewed gender ratio, spatial separation and resource utilization. Female willows would suffer fiercer competition for space by males with the increased soil N, which would result in the gender ratio alteration. Therefore, gender ratio of willows is likely to convert to gender balance from female-biased with long-term N deposition in the future.
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http://dx.doi.org/10.1093/treephys/tpab083DOI Listing
June 2021

Traditional Chinese medicine shenhuang granule in patients with severe/critical COVID-19: A randomized controlled multicenter trial.

Phytomedicine 2021 Aug 28;89:153612. Epub 2021 May 28.

LongHua Hospital, Shanghai University of Traditional Chinese Medicine, 725 Wanping South Road, Xuhui District, Shanghai 200032, China; Leishenshan Hospital of Wuhan, Wuhan, 430200, Hubei, China. Electronic address:

Background: Coronavirus disease 2019 (COVID-19) is still a pandemic, with a high mortality rate in severe/critical cases. Therapies based on the Shenghuang Granule have proved helpful in viral infection and septic shock.

Hypothesis/purpose: The objective of the current study was to compare the efficacy and safety of the traditional Chinese medicine, Shenhuang Granule, with standard care in hospitalized patients with severe/critical COVID-19.

Study Design And Methods: This was an open-label, multicenter, randomized, controlled clinical trial. At 4 medical centers, a total of 111 severe/critical patients were randomly assigned to receive Shenhuang Granule (SHG group) twice a day for 14 days, in addition to standard care, or to receive standard care alone (Control group). The maximal follow up time was 75 days. The clinical endpoint was clinical improvement and mortality.

Results: 54 patients were assigned to the control group and 57 to the SHG group. The overall mortality was 75.9% (41/54) in the control group, and 38.6% (22/57) in the SHG group (p < 0.01 vs. control). The post hoc analysis showed that in the severe category, the mortality of the control group vs. the SHG group was 58.8% (10/17) vs. 5.3% (1/19) (p < 0.01); while in the critical category, it was 83.8% (31/37) vs. 55.3% (21/38) (p < 0.05). In the severe category, the mortality of patients who eventually received an invasive ventilator in the control vs. the SHG group was 58.8% (10/17) vs. 0 (0/19) (p < 0.01). Administration of SHG was associated with increased lymphocytes and decreased adverse events.

Conclusion: Shenhuang Granule is a promising integrative therapy for severe and critical COVID-19.
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http://dx.doi.org/10.1016/j.phymed.2021.153612DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8161732PMC
August 2021

Analytical Consideration for the Maximum Spreading Factor of Liquid Droplet Impact on a Smooth Solid Surface.

Langmuir 2021 Jun 11;37(24):7582-7590. Epub 2021 Jun 11.

Key Laboratory of Advanced Reactor Engineering and Safety of Ministry of Education, Collaborative Innovation Center of Advanced Nuclear Energy Technology, Institute of Nuclear and New Energy Technology, Tsinghua University, Beijing 100084, China.

Based on the energy conservation approach, this study develops a universal model to predict the maximum spreading factor of liquid droplet impact on a smooth solid surface. Validated with the present simulations and experiments in the literature, this model effectively overcomes the limitation of previous models in the viscous regime and greatly reduces the computing errors from over 30% to below 6%. It is demonstrated that the underestimated maximum spreading factor by previous models results from the overestimation of viscous dissipation. By replacing the conventional model of spreading time, = 8/3, with a more precise one, = 1.47, the formulation to compute the viscous dissipation of entire spreading is improved. Finally, we examine the applicability of present model in the capillary regime and good performance is also shown.
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http://dx.doi.org/10.1021/acs.langmuir.1c01076DOI Listing
June 2021

DNA methyltransferase 1 inhibits O-methylguanine-DNAmethyl-transferase-mediated cell growth and metastasis of hypopharyngeal squamous carcinoma.

Arch Oral Biol 2021 Aug 19;128:105160. Epub 2021 May 19.

Department of Otorhinolaryngology Head and Neck Surgery, The Affiliated Yantai Yuhuangding Hospital of Qingdao University, Yantai, Shandong, 264000, China. Electronic address:

Objective: To explore the role of DNA methyltransferase 1 (DNMT1) in development and progression of hypopharyngeal squamous carcinoma.

Design: A total of 32 hypopharyngeal squamous carcinoma biopsy samples and 20 normal tissue specimens were collected. Immunohistochemical staining, quantitative real-time polymerase chain reaction, and Western blot were performed for expression analysis. The mRNA and protein expression in the specimens and subcellular localization were analyzed. hypopharyngeal squamous carcinoma cells (FaDu) were used for small interfering RNA of DNMT1, and proliferation, cell cycle, and apoptosis were determined in the transfected cells. Furthermore, metastatic ability and methylation status of O-methylguanine-DNAmethyl-transferase (MGMT) promoter was assessed.

Results: Our results showed that DNMT1 was overexpressed, while MGMT was down expressed in hypopharyngeal squamous carcinoma. DNMT1 overexpression and MGMT down expression were significantly associated with poorly differentiated tumors, lymph node metastasis, and clinical stage. DNMT1 and MGMT were majorly distributed in the nucleus. Furthermore, knockdown of DNMT1 inhibited proliferation and metastasis, induced apoptosis and G1 phase arrest in FaDu cells, and upregulated MGMT expression to reverse methylation status of MGMT promoter.

Conclusions: This study for the first time demonstrated the clinical value and the role of DNMT1 and MGMT in the biological function of hypopharyngeal squamous carcinoma. This work suggested that DNMT1 might serve as a potential therapeutic target for patients with hypopharyngeal squamous carcinoma.
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http://dx.doi.org/10.1016/j.archoralbio.2021.105160DOI Listing
August 2021

Radical-mediated sulfonyl alkynylation, allylation, and cyanation of propellane.

Chem Commun (Camb) 2021 Jun;57(49):6066-6069

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China. and Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Bicyclo[1.1.1]pentane (BCP) is widely applied as the bioisostere for aryl, internal alkynes, and tert-butyl groups in medicinal chemistry. We herein disclose an efficient and practical preparation of sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives through a novel radical-mediated difunctionalization of propellane. The radical alkynylation, allylation, and cyanation processes readily proceed under mild photochemical conditions. The synthetic method features broad functional group tolerance, high product diversity, gram-scale preparation, and excellent atom-economy.
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http://dx.doi.org/10.1039/d1cc02249kDOI Listing
June 2021

Prognostic Value of Autophagy, Microsatellite Instability, and Mutations in Colorectal Cancer.

J Cancer 2021 20;12(12):3515-3528. Epub 2021 Apr 20.

Department of Pathology, Affiliated Cancer Hospital of Zhengzhou University, Henan Cancer Hospital, 127 Dongming Road, Zhengzhou 450008, China.

Autophagy plays pivotal role in various tumors, including colorectal cancer (CRC). Microsatellite instability (MSI) and mutations are also involved in response to the adjuvant therapy of CRC. We aimed to investigate the relationships among autophagy, mutations, MSI, clinicopathological parameters, and prognosis in CRC patients. We tested 200 CRC tumors for autophagy-related protein expression (Beclin 1 and LC3), MSI status, and mutations. Expression of Beclin 1 and LC3 was higher in CRC, with Beclin 1 significantly correlating with the depth of invasion, whereas LC3 was not associated with clinicopathological parameters. Patients expressing the LC3 proteins experienced a shorter overall survival (OS) after surgery with adjuvant therapy, especially in the MSS/L-CRC subgroup and the mutated subgroup. MSS/L-CRC patients with KRAS mutations positively expressed the LC3 protein and suffered a shorter OS than LC3 non-expressing patients. In CRC patients who received either capecitabine or capecitabine combined with oxaliplatin post-surgery, the positive expression of LC3 correlated with worse OS compared to patients who did not express LC3. Sequencing showed BRCA1/2 as the most variant genes in all patients. Nevertheless, deleterious variations were more frequent in patients with MSI-H CRC. High LC3 protein expression shows a certain prognostic value in CRC patients. LC3, the MSI status, and mutations must be considered when selecting an adjuvant therapy for CRC. The detection of these indexes is of great significance to identify high-risk patients who would benefit from autophagy-related anticancer drugs or help to explore more effective treatment options for patients who are resistant to conventional chemotherapy or relapse.
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http://dx.doi.org/10.7150/jca.51430DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8120188PMC
April 2021

LCT-3d Induces Oxidative Stress-Mediated Apoptosis by Upregulating Death Receptor 5 in Gastric Cancer Cells.

Front Oncol 2021 16;11:658608. Epub 2021 Apr 16.

Key Laboratory of Advanced Technology for Drug Preparation, Ministry of Education, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, China.

Gastric cancer is a global health problem. In this study, we investigate the role of a novel Indole derivative, named LCT-3d, in inhibiting the growth of gastric cancer cells by MTT assay. The Western blotting results showed that LCT-3d modulated the mitochondrial-related proteins and Cleaved-Caspases 3/9, to induce cell apoptosis. The up-regulation of Death receptor 5 (DR5) in MGC803 cells was observed with LCT-3d treatment. Knockdown of DR5 on MGC803 cells partially reversed the LCT-3d-induced mitochondrial apoptosis. The level of Reactive Oxygen Species (ROS) in MGC803 cells was increased with LCT-3d treatment and could be blocked with the pretreatment of the ROS inhibitor N-Acetylcysteine (NAC). The results demonstrate that the elevating ROS can up-regulate the expression of DR5, resulting in apoptosis mitochondrial pathway. Although the nuclear factor erythroid-2 related factor 2 (Nrf2) pathway served an important role in protecting gastric cancer cells against the injury of ROS, it can't reverse LCT-3d-induced cell apoptosis. Taken together, our study showed that LCT-3d induced apoptosis DR5-mediated mitochondrial apoptotic pathway in gastric cancer cells. LCT-3d could be a novel lead compound for development of anti-cancer activity in gastric cancer.
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http://dx.doi.org/10.3389/fonc.2021.658608DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8085419PMC
April 2021

Structural characterization and physicochemical properties of starch from four aquatic vegetable varieties in China.

Int J Biol Macromol 2021 Mar 15;172:542-549. Epub 2021 Jan 15.

School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, Jiangsu, PR China.

Nelumbo nucifera Gaertn., Eleocharis dulcis, Sagittaria sagittifolia L., and Trapa bispinosa Roxb. are common aquatic vegetables that are rich in starch. Starches from these four aquatic vegetables and their applications in edible films were studied to facilitate full use of starch resources. Significant differences in transparency, freeze-thaw stability, water solubility index, swelling power, water and oil absorption capacities, starch particle morphology, and rheology were observed among the starches from these four aquatic vegetables. All starches exhibited a typical "A" type diffraction pattern. N. nucifera, E. dulcis, and S. sagittifolia starches have similar thermal properties, while T. bispinosa starch has a higher gelatinization temperature. S. sagittifolia starch film has the highest transparency and lower WVP and water solubility. These results will promote the development of products based on starch obtained from aquatic vegetables.
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http://dx.doi.org/10.1016/j.ijbiomac.2021.01.078DOI Listing
March 2021

Novel coronavirus pneumonia (COVID-19) combined with Chinese and Western medicine based on "Internal and External Relieving -Truncated Torsion" strategy.

Medicine (Baltimore) 2020 Dec;99(51):e23874

Shanghai University of Traditional Chinese Medicine, NO.1200 Cai Lun Road, Zhangjiang Hi-Tech Park, Pudong New Area, Shanghai.

Introduction: The outbreak of novel coronavirus disease 2019 (COVID-19) has caused a global pandemic since December 2020. It has not only associated with physiological disorder but also with psychological distress and symptoms of mental illness. Whether the vaccines and antivirals can provide protects remains unknown. Traditional Chinese medicine (TCM) is recommended as an alternative and significant way of preventing and treating COVID-19 in China. However, few studies have assessed the benefits of this treatment and mental health after they recover. Our study is designed to investigate effects and safety when using TCM on the course of this disease and the impact of COVID-19 on pandemic-related anxiety.

Method: For this prospective cohort study, we will enroll 300 COVID-19 patients aged 18 to 80 years at 4 centers. We divide them into 2 groups, according to whether they use Baidu Jieduan Granule at a ratio of 1:1. We will compare treatments combined Baidu Jieduan Granule with conventional Western medicine (experimental group) vs treatment of conventional Western medicine only (control group). The basic information of patients including demographic, general condition, primary diseases, and complications will be assessed. Related examines will be conducted at 1, 3, 5, 7, and 14 days. The primary outcomes are clinical outcome. A follow-up time of 1 year (to June 30, 2021) allow us to evaluate the psychiatric disorder after recovery. We will monitor adverse events throughout the trial.

Discussion: It will be the first prospective cohort study which uses Baidu Jieduan Granule, based on the innovation traditional Chinese medicine strategy of " Internal and External Relieving -Truncated Torsion " to treat the common type of COVID-19. The result of this study may provide evidence-based recommendations of TCM for treatment and psychological distress or symptoms of mental illness of the common type of COVID-19.
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http://dx.doi.org/10.1097/MD.0000000000023874DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7748371PMC
December 2020

Genome-wide analysis of PmTCP4 transcription factor binding sites by ChIP-Seq during pistil abortion in Japanese apricot.

Plant Genome 2020 11 19;13(3):e20052. Epub 2020 Aug 19.

Laboratory of Fruit Tree Biotechnology, College of Horticulture, Nanjing Agricultural University, Nanjing, China.

The TCP4 transcription factor plays an important role in plant growth and development, especially in flower development. PmTCP4 is involved in the process of pistil abortion in Japanese apricot, but its molecular mechanism, particularly the DNA binding sites and co-regulatory genes, are quite unknown. Therefore, to identify the genome-wide binding sites of PmTCP4 transcription factors and their co-regulatory genes, chromatin immunoprecipitation sequencing (ChIP-Seq) was carried out. ChIP-Seq data produced the maximum enriched peaks in two Japanese apricot cultivars 'Daqiandi' (DQD) and 'Longyan' (LY), which showed that the majority of DNA-protein interactions are relevant and have a significant function in binding sites. Moreover, 720 and 251 peak-associated genes regulated by PmTCP4 were identified in DQD and LY, respectively, and most of them were involved in the flower and pistil development process. Furthermore, Kyoto Encyclopedia of Genes and Genomes (KEGG) analysis showed that photosynthesis and oxidative phosphorylation were the most enriched pathways in both cultivars and all identified genes related to these pathways were down-regulated. This study will provide a reference for a better understanding of the PmTCP4 regulatory mechanism during pistil abortion in Japanese apricot.
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http://dx.doi.org/10.1002/tpg2.20052DOI Listing
November 2020

Heterocyclization Reagents for Rapid Assembly of N-Fused Heteroarenes from Alkenes.

Angew Chem Int Ed Engl 2021 02 15;60(7):3714-3719. Epub 2020 Dec 15.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.

N-Fused heterocycles are of particular use and upmost importance in multiple fields. Herein, we disclose a conceptually new approach for the rapid assembly of N-fused heteroarenes from alkenes. A portfolio of strategically designed heterocyclization reagents are readily prepared for the cascade reaction. A plethora of N-fused heteroarenes including seven types of heterocyclic core are furnished. The protocol features a broad functional-group compatibility and high product diversity, and provides a practical tool for late-stage heteroarene elaboration.
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http://dx.doi.org/10.1002/anie.202013089DOI Listing
February 2021

Metal-Free Radical-Mediated C(sp)-H Heteroarylation of Alkanes.

Org Lett 2020 Oct 24;22(19):7450-7454. Epub 2020 Sep 24.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.

Herein we disclose a metal-free, N/O-centered radical-promoted Minisci reaction, in which the coupling of various heteroarenes with simple alkanes proceeds under mild conditions. The reaction conditions are neutral; no extra acid is added to preactivate N-heteroarenes in the Minisci reaction. The N-/O-centered radicals are generated directly from amide (TsNHMe) or alcohol (CFCHOH) under visible-light irradiation. This green and eco-friendly synthetic process may find potential use in medicinal chemistry.
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http://dx.doi.org/10.1021/acs.orglett.0c02475DOI Listing
October 2020

A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27.

Eur J Med Chem 2020 Nov 7;206:112708. Epub 2020 Aug 7.

Key Laboratory of Advanced Technology for Drug Preparation, Ministry of Education, School of Pharmaceutical Sciences, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, 450001, China; Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Zhengzhou University, No. 100, KeXueDaDao, Zhengzhou, 450001, China; State Key Laboratory of Esophageal Cancer Prevention & Treatment, Zhengzhou University, Zhengzhou, Henan Province, 450052, PR China. Electronic address:

Chromosome region maintenance 1 (CRM1) is the sole nuclear exporter of several tumor suppressor, a growth regulatory protein as an attractive cancer drug target. In the present work, a novel CRM1 degrader was discovered from newly synthesized α, β-unsaturated-δ-lactone based on a natural product Goniothalamin. It induces apoptosis of both MGC803 and HGC27 cell lines via degrading CRM1. Selective inhibition was observed for the proliferation of gastric cancer cell lines MGC803, HGC27 comparing to Human Gastric Mucosal Epithelial Cell Line (GES1). For the first time, CRM1 inhibitor or degrader inducing apoptosis in gastric carcinoma was investigated.
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http://dx.doi.org/10.1016/j.ejmech.2020.112708DOI Listing
November 2020

Radical-Mediated Remote Functional Group Migration.

Authors:
Xinxin Wu Chen Zhu

Acc Chem Res 2020 08 24;53(8):1620-1636. Epub 2020 Jul 24.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.

Alkenes are ubiquitous in natural products and are extensively used as synthetic feedstocks in multiple fields including organic synthesis, medicinal chemistry, and materials science. Radical-mediated difunctionalization of alkenes provides a powerful tactic for alkene utilization. Despite the considerable progress made in the past several decades, state-of-the-art methods are highly dependent upon activated alkenes in which a proximal group with a π-electron system (e.g., aryl, carbonyl, and heteroatom) is requisite to stabilize the nascent alkyl radical intermediate via p-π conjugation or p orbitals of the heteroatom. In contrast, the transformation of unactivated alkenes, such as aliphatic alkenes, remains challenging.To overcome this obstacle, we have recently disclosed the strategy of intramolecular distal functional group migration (FGM), which has been efficiently applied in radical difunctionalization of unactivated alkenes. A portfolio of functional groups, such as cyano, heteroaryl, oximino, formyl, and alkynyl groups, showcase the excellent migratory aptitude. Mechanistically, after the addition of an extrinsic radical to the alkene, the newly formed active alkyl radical is rapidly captured by the intramolecular migratory group to generate a cyclic intermediate. Subsequent cleavage of the cyclic C-C bond of the intermediate leads to the functionalized product through the FGM process. Based on the strategy of FGM, a set of elusive difunctionalizations of unactivated alkenes have been accomplished (Part A).Alongside this research, an upgraded highly efficient synthetic strategy, "dock-migration," is created for intermolecular difunctionalization of alkenes. A diversity of sulfone-based dual-function reagents are developed. The intermolecular transformation is initiated by docking the dual-function reagent to the alkene, followed by intramolecular migration of the functional group. Compared to the original FGM protocol, the scope of alkenes is significantly extended from the strategically placed tertiary alcohol-substituted alkenes to general alkenes. Both activated and unactivated alkenes are well tolerated. By this approach, radical-mediated fluoroalkylheteroarylation, fluoroalkylalkynylation, and alkylation of alkenes have been achieved (Part B).Direct elaboration of C-H bonds into the targeted functional groups represents one of the most ideal and straightforward methods for molecular functionalization. The FGM strategy proves to be an ingenious tool for radical-mediated functionalization of remote unactivated C(sp)-H bonds. Based on the FGM process, we have accomplished: (a) remote C(sp)-H heteroarylation and cyanation of unprotected alcohols via the cascade of alkoxy radical-enabled hydrogen atom transfer (HAT) and intramolecular functional group (e.g., heteroaryl, cyano) migration, and (b) distal C(sp)-H vinylation of propargylic alcohols through consecutive alkenyl radical-promoted HAT process and subsequent alkenyl migration (Part C).
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http://dx.doi.org/10.1021/acs.accounts.0c00306DOI Listing
August 2020

Radical-Mediated Distal Ipso-Migration of O/S-Containing Heteroaryls and DFT Studies for Migratory Aptitude.

Org Lett 2020 08 23;22(15):5947-5952. Epub 2020 Jul 23.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.

Herein we describe an efficient distal ipso-migration of - and -containing heteroaryls and the radical heteroarylation of unactivated alkenes. The migration is triggered by various fluoroalkyl radicals, leading to valuable multifunctionalized ketones. The comparisons of migratory aptitude for -/-containing heteroaryls are comprehensively investigated. The origin of the chemoselective migration could be partially attributed to the discrepancy in the energy level of the LUMO of each heteroaryl group.
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http://dx.doi.org/10.1021/acs.orglett.0c02030DOI Listing
August 2020

Shenhuang granule in the treatment of severe coronavirus disease 2019 (COVID-19): study protocol for an open-label randomized controlled clinical trial.

Trials 2020 Jun 24;21(1):568. Epub 2020 Jun 24.

Department of Emergency Internal Medicine, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, No.1095 Jie Fang Avenue, Hankou, Wuhan, 430030, Hubei, China.

Background: Currently, coronavirus disease 2019 (COVID-19) is continuously and rapidly circulating, causing heavy damage on public health. No effective antiviral treatment has been proved thus far. Traditional Chinese medicine (TCM) has been widely applied in the treatment of a variety of infection diseases in China, hoping to produce clinical effects and reduce the use of antibiotics and glucocorticoid. The aim of this study is to evaluate the efficacy and safety of Shenhuang granule in treatment of severe COVID-19.

Methods/design: This multicenter, open-label randomized controlled trial is conducted in 160 participants with severe COVID-19. The participants will be randomly (1:1) divided into treatment group or control group. All participants are given standard therapy at the same time. The experiment will receive Shenhuang granule treatment twice a day for 14 days. The clinical indicators of patients will be assessed at baseline and at 3, 5, 7, and 14 days after treatment initiation. The primary outcome is 14-day clinical outcome. Adverse events will be monitored throughout the trial.

Discussion: This will be the first randomized controlled trial, which evaluate the effect of Shenhuang granule in patients with severe COVID-19 in China. The results of this trial may not only provide evidence-based recommendations to clinicians to treat severe COVID-19, but also enrich the theory and practice of TCM in treating infectious diseases.

Trial Registration: Chinese Clinical Trial Registry, ChiCTR2000029777. Registered on 13 February 2020.
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http://dx.doi.org/10.1186/s13063-020-04498-6DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7312108PMC
June 2020

Dynamic Monitoring of sTREM-1 and Other Biomarkers in Acute Cholangitis.

Mediators Inflamm 2020 15;2020:8203813. Epub 2020 May 15.

Affiliated Hangzhou First People's Hospital, Zhejiang Chinese Medical University, Hangzhou, China.

Background: Sepsis is a common complication of acute cholangitis (AC), which is associated with a high mortality rate. Our study is aimed at exploring the significance of white blood cell (WBC), C-reactive protein (CRP), procalcitonin (PCT), soluble triggering receptor expressed on myeloid cells 1 (sTREM-1), and temperature (T) alone or combined together in early identification and curative effect monitoring of AC with or without sepsis.

Methods: 65 consecutive cases with AC and 76 control cases were enrolled. They were divided into three groups: Group A (AC with sepsis), Group B (AC without sepsis), and Group C (inpatients without AC or other infections). The levels of WBC, CRP, PCT, sTREM-1, and temperature were measured dynamically. The study was carried out and reported according to STARD 2015 reporting guidelines.

Results: CRP had the highest AUC to identify AC from individuals without AC or other infections (AUC 1.000, sensitivity 100.0%, specificity 100.0%, positive predictive value 100.0%, and negative predictive value 100.0%). Among various single indexes, PCT performed best (AUC 0.785, sensitivity 75.8%, specificity 72.2%, positive predictive value 68.7%, and negative predictive value 78.8%) to distinguish sepsis with AC, while different combinations of indexes did not perform better. From day 1 to day 5 of hospitalization, the levels of sTREM-1 in Group A were the highest, followed by Groups B and C ( < 0.05); on day 8, sTREM-1 levels in Groups A and B declined back to normal. However, other index levels among three groups still had a significant difference on day 10. Both in Groups A and B, sTREM-1 levels declined fast between day 1 and day 2 ( < 0.05).

Conclusions: CRP is the best biomarker to suggest infection here. PCT alone is sufficient enough to diagnose sepsis with AC. sTREM-1 is the best biomarker to monitor patients' response to antimicrobial therapy and biliary drainage.
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http://dx.doi.org/10.1155/2020/8203813DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7245684PMC
July 2021

Cross-Feeding between Members of spp. and spp. Drives Quinoline-Denitrifying Degradation in a Hypoxic Bioreactor.

mSphere 2020 04 29;5(2). Epub 2020 Apr 29.

State Key Laboratory of Microbial Metabolism, Shanghai Jiao Tong University, Shanghai, China

The complex bacterial community in a quinoline-degrading denitrifying bioreactor is predominated by several taxa, such as and However, it remains unclear how the interactions between the different bacteria mediate quinoline metabolism under denitrifying conditions. In this study, we designed a sequence-specific amplification strategy to isolate the most predominant bacteria and obtained four strains of , a representative of a key member in the bioreactor. Tests on these isolates demonstrated that all were unable to degrade quinoline but efficiently degraded 2-hydroxyquinoline, the hypothesized primary intermediate of quinoline catabolism, under nitrate-reducing conditions. However, another isolate, sp. YF3, corresponding to the second most abundant taxon in the same bioreactor, was found to degrade quinoline via 2-hydroxyquinoline. The end products and removal rate of quinoline by isolate YF3 largely varied according to the quantity of available oxygen. Specifically, quinoline could be converted only to 2-hydroxyquinoline without further transformation under insufficient oxygen conditions, e.g., less than 0.5% initial oxygen in the vials. However, resting YF3 cells aerobically precultured in medium with quinoline could anaerobically convert quinoline to 2-hydroxyquinoline. A two-strain consortium constructed with isolates from (R2) and (YF3) demonstrated efficient denitrifying degradation of quinoline. Thus, we experimentally verified that the metabolic interaction based on 2-hydroxyquinoline cross-feeding between two predominant bacteria constitutes the main quinoline degradation mechanism. This work uncovers the mechanism of quinoline removal by two cooperative bacterial species existing in denitrifying bioreactors. We experimentally verified that the second most abundant taxon, , played a role in degrading quinoline to 2-hydroxyquinoline, while the most abundant taxon, , degraded 2-hydroxyquinoline. Metabolites from further served to provide metabolites for Hence, an ecological guild composed of two isolates was assembled, revealing the different roles that keystone organisms play in the microbial community. This report, to the best of our knowledge, is the first on cross-feeding between the initial quinoline degrader and a second bacterium. Specifically, the quinoline degrader () did not benefit metabolically from quinoline degradation to 2-hydroxyquinoline but instead benefited from the metabolites produced by the second bacterium () when degraded the 2-hydroxyquinoline. These results could be a significant step forward in the elucidation of the microbial mechanism underlying quinoline-denitrifying degradation.
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http://dx.doi.org/10.1128/mSphere.00246-20DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7193041PMC
April 2020

Polarity Umpolung Strategy for the Radical Alkylation of Alkenes.

Angew Chem Int Ed Engl 2020 05 11;59(21):8195-8202. Epub 2020 Mar 11.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.

Free radical mediated alkylation of alkenes is a challenging and largely unmet goal. Disclosed here is a conceptually novel "polarity umpolung" strategy for radical alkylation of alkenes using a portfolio of easily accessed, difunctional alkylating reagents. This strategy is achieved by substituting inherently nucleophilic alkyl radicals with electrophilic sulfone-bearing surrogates, thus inverting the usual mode of reactivity. Along with alkylation, either an heteroaryl or oximino group is concurrently incorporated into the alkenes by a consecutive docking and migration process, leading to valuable products. The reaction displays a broad functional-group tolerance under mild reaction conditions. The protocol opens new vistas for the late-stage modification of complex natural products and drug molecules containing alkene moieties.
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http://dx.doi.org/10.1002/anie.201915837DOI Listing
May 2020

Radical-mediated C-C cleavage of unstrained cycloketones and DFT study for unusual regioselectivity.

Nat Commun 2020 02 3;11(1):672. Epub 2020 Feb 3.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, 215123, Suzhou, Jiangsu, China.

The C-C σ-bond activation of unstrained cycloketones represents an ingenious and advanced technique in synthetic chemistry, but it remains a challenging area which has been largely underexplored. Herein we report an efficient strategy for the direct C-C cleavage of cyclohexanones and cyclopentanones. The cyclic C-C σ-bond is readily cleaved under mild conditions with the aid of an in situ formed side-chain aryl radical. Density functional theory calculations are carried out to shed light on the unusual regioselectivity of C-C bond cleavage. The reaction affords a variety of structurally diverse 3-coumaranones and indanones that widely exist in natural products and bioactive molecules, illustrating the synthetic value of this method.
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http://dx.doi.org/10.1038/s41467-020-14435-5DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6997357PMC
February 2020

DNA methylation of LDOX gene contributes to the floral colour variegation in peach.

J Plant Physiol 2020 Mar - Apr;246-247:153116. Epub 2020 Jan 15.

College of Horticulture, Nanjing Agricultural University, No. 1 Weigang, Nanjing 210095, China. Electronic address:

Peach is an important fruit and ornamental plant around the globe. Variegation in flowers often captures consumers' attention, and variegated plants are of high ornamental value. To determine the relationship between DNA methylation and phenotype, we obtained the first single-nucleotide resolution DNA methylation of variegation cultivars in peach through bisulfite sequencing. In this study, a similar methylation rate of 12.90 % in variegated flower buds (VF) and 11.96 % in red flower buds (RF) was determined. The methyl-CG (mCG) was the main context in both samples. We identified 503 differentially methylated regions (DMRs) in all chromosomes. These DMRs were focused on 96 genes and 156 promoters. Associated with the transcriptional and proteome analysis, 106 differently expressed genes and 52 different proteins had varying degrees of methylation. Silent genes exhibited higher methylation levels than expressed genes. The methylation state of the leucoanthocyanidin dioxygenase (LDOX) promoter in VF was higher than RF at flower stages 2 (FS2) based on bisulfite sequencing PCR (BSP) results. Moreover, further experiments showed LDOX gene expression and enzyme activity in RF was higher than VF. The DNA methylation trend consisted of the gene expression and flower colour phenotype. Several cis-acting regulatory elements on BSP sequences were involved in phytohormones, transcription factors, and light responsiveness, which could affect gene expression. The higher level of LDOX gene expression promoted synthesis of colourful anthocyanidins, which caused red spots on the petal. Together, this study identified the context and level of methylation at each site with bisulfite sequencing (BS). These results are helpful in uncovering the mechanism of variegated flower petal formation in peach.
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http://dx.doi.org/10.1016/j.jplph.2020.153116DOI Listing
August 2020

Radical Monofluoroalkylative Alkynylation of Olefins by a Docking-Migration Strategy.

Angew Chem Int Ed Engl 2019 12 21;58(49):17646-17650. Epub 2019 Oct 21.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.

A radical-mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking-migration sequence, affording a vast array of valuable fluoroalkyl-substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late-stage alkynylation.
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http://dx.doi.org/10.1002/anie.201910514DOI Listing
December 2019

Radical-Mediated Heck-Type Alkylation: Stereoconvergent Synthesis of Functionalized Polyenes.

Org Lett 2019 Sep 3;21(18):7568-7572. Epub 2019 Sep 3.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science , Soochow University , 199 Ren-Ai Road , Suzhou , Jiangsu 215123 , China.

The stereospecific synthesis of polyenes is of great synthetic value. Disclosed herein is a new, efficient, stereoconvergent approach for the synthesis of functionalized polyenes via a radical-mediated Heck-type alkylation. The easily accessed and -mixed alkenes are harnessed as starting material, leading to a unique stereoisomer of polyenes. In addition, the transformation features mild reaction conditions and broad functional group compatibility. A variety of valuable 1,3-dienes and 1,3,5-trienes are afforded in useful yields.
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http://dx.doi.org/10.1021/acs.orglett.9b02838DOI Listing
September 2019
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