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Mol Cell Proteomics 2021 Apr 13:100081. Epub 2021 Apr 13.

Department of Chemistry, University of Wisconsin, Madison, WI, 53705, USA; School of Pharmacy, University of Wisconsin, Madison, WI, 53705, USA. Electronic address:

As the body fluid that directly interchanges with the extracellular fluid of central nervous system (CNS), cerebrospinal fluid (CSF) serves as a rich source for CNS-related disease biomarker discovery. Extensive proteome profiling has been conducted for CSF, but studies aimed at unraveling site-specific CSF N-glycoproteome are lacking. Initial efforts into site-specific N-glycoproteomics study in CSF yield limited coverage, hindering further experimental design of glycosylation-based disease biomarker discovery in CSF. Read More

J Am Chem Soc 2021 Apr 16. Epub 2021 Apr 16.

Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Avenue, Columbus, Ohio 43210, United States.

Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Read More

J Colloid Interface Sci 2021 Mar 29;596:225-232. Epub 2021 Mar 29.

College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao, Shandong 266590, China. Electronic address:

Glycoproteins play crucial roles in many biological events such as protein folding, information transmission, nerve conduction, and molecular recognition. Some glycoproteins serve as disease biomarkers in clinical settings. However, selective detection of glycoprotein often faces great challenges, owing to its low abundance in complex biological samples. Read More

J Agric Food Chem 2021 Apr 13. Epub 2021 Apr 13.

School of Pharmaceutical Sciences, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China.

Brassinosteroids (BRs) are natural, nontoxic, non-hazardous, biosafe, and eco-friendly plant hormones, possessing diverse pharmacological activities. However, little is known about the type and content of BRs in frequently consumed plant-derived foodstuffs because of their low abundance and high abundance of interference. In this study, a selective, accurate, and sensitive method based on the online solid-phase extraction using the boronic acid-functionalized Scholl-coupling microporous polymer was developed for the analysis of BRs in plant-derived foodstuffs. Read More

Future Med Chem 2021 Apr 13. Epub 2021 Apr 13.

Université Paris-Saclay, CNRS, Institut de chimie moléculaire et des matériaux d'Orsay, Orsay, 91405, France.

Org Lett 2021 Apr 12. Epub 2021 Apr 12.

University of Strasbourg, CNRS, ISIS UMR 7006, 8 Allée Gaspard Monge, 67000 Strasbourg, France.

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr). Read More

ACS Sens 2021 Apr 12. Epub 2021 Apr 12.

School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, B15 2TT, United Kingdom.

Boronic acids can reversibly bind diols, a molecular feature that is ubiquitous within saccharides, leading to their use in the design and implementation of sensors for numerous saccharide species. There is a growing understanding of the importance of saccharides in many biological processes and systems; while saccharide or carbohydrate sensing in medicine is most often associated with detection of glucose in diabetes patients, saccharides have proven to be relevant in a range of disease states. Herein the relevance of carbohydrate sensing for biomedical applications is explored, and this review seeks to outline how the complexity of saccharides presents a challenge for the development of selective sensors and describes efforts that have been made to understand the underpinning fluorescence and binding mechanisms of these systems, before outlining examples of how researchers have used this knowledge to develop ever more selective receptors. Read More

ACS Appl Nano Mater 2021 Mar 19;4(3):2866-2875. Epub 2021 Feb 19.

Division of Pure and Applied Biochemistry, Department of Chemistry, Lund University, Box 124, 22100 Lund, Sweden.

Dendritic fibrous nanosilica (DFNS) has very high surface area and well-defined nanochannels; therefore, it is very useful as supporting material for numerous applications including catalysis, sensing, and bioseparation. Due to the highly restricted space, addition of molecular ligands to DFNS is very challenging. This work studies how ligand conjugation in nanoscale pores in DFNS can be achieved through copper-catalyzed click reaction, using an optional, in situ synthesized, temperature-responsive polymer intermediate. Read More

J Fluor Chem 2021 May 21;245. Epub 2021 Feb 21.

Azrieli Centre for Neuro-Radiochemistry, Brain Health Imaging Centre, Centre for Addiction and Mental Health, Toronto, ON, M5T 1R8, Canada.

Glycogen synthase kinase 3 (GSK-3) is an enzyme that is dysregulated in oncology neurodegeneration, neuroinflammation and several mental health illnesses. As such, GSK-3 is a long-sought after target for positron emission tomography (PET) imaging and therapeutic intervention. Herein, we report on the development and radiofluorination of two oxazole-4-carboxamides, including one bearing a non-activated aromatic ring. Read More

Curr Microbiol 2021 Apr 10. Epub 2021 Apr 10.

Medical Microbiology Research Center, Qazvin University of Medical Science, Qazvin, Iran.

One of the mechanisms of Klebsiella pneumoniae and Escherichia coli resistance to β-lactam antibiotics is the production of β-lactamase enzymes. Among these are the AmpC β-lactamases, which confer resistance to a class of antibiotics. However, little is known about the AmpC β-lactamases of K. Read More

Bioorg Med Chem 2021 Mar 23;38:116114. Epub 2021 Mar 23.

College of Life Science, Nanjing Normal University, No. 1 Wenyuan Road, Nanjing 210037, PR China. Electronic address:

Valine-containing protein (VCP) is a member of the adenosine triphosphate family involved in a variety of cellular activities. VCP/p97 is capable of maintaining protein homeostasis and mediating the degradation of misfolded polypeptides by the ubiquitin-proteasome system (UPS). In this manuscript, a series of novel p97 inhibitors with pyrimidine as core structure were designed, synthesized and biologically evaluated. Read More

Org Lett 2021 Apr 8. Epub 2021 Apr 8.

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.

Upon application of a multicomponent Petasis reaction, a broad range of H-sulfoximines and boronic acids react with glyoxalic acid to afford the corresponding 2-substituted acetic acids with N-bound sulfoximidoyl groups. The protocol features excellent yields under ambient, metal-free conditions and short reaction times. Furthermore, the applicability of 2-sulfoximidoyl acetic acids as building blocks for synthesizing sulfoximine-based benzodiazepine analogues was demonstrated. Read More

Org Lett 2021 Apr 8;23(8):3004-3009. Epub 2021 Apr 8.

School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.

The assembly of guanosine and boronic acids produces anionic hydrogels (G-B hydrogels) that mimic the topology of the DNA G-quadruplex. We herein demonstrate an unconventional approach of using the G-B hydrogel as a supramolecular template that assembles the irreversible formation of DNA G-quadruplex-selective 1,4-triazole ligands from a pool of alkyne-azide building blocks. These generated ligands could also stabilize and strengthen the gel assembly. Read More

Photochem Photobiol Sci 2020 May 27;19(5):722-725. Epub 2020 Oct 27.

Friedrich-Alexander University Erlangen-Nuernberg, Department of Chemistry and Pharmacy, Organic Chemistry II, Nikolaus-Fiebiger Str. 10, 91058, Erlangen, Germany.

The synthesis of ten ortho-fused PAHs bearing boronic pinacol ester groups (BPin) is reported. The products are obtained via modification of Mallory photocyclization in 45-99% yields. Among them are examples of highly strained molecules such as [4]helicene derivatives with BPin substituents in the cavity. Read More

J Org Chem 2021 Apr 8;86(8):5973-5982. Epub 2021 Apr 8.

Laboratory of Organic Chemistry for Drug Development and Medical Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, Japan.

Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2- glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of -vicinal diols in glycosyl acceptors. Read More

Org Lett 2021 Apr 6;23(8):3207-3210. Epub 2021 Apr 6.

Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.

A direct and site-specific alkylation of (sp)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could be obtained in good yields. Read More

J Med Chem 2021 Apr 6. Epub 2021 Apr 6.

Genomics Institute of the Novartis Research Foundation, 10675 John J. Hopkins Dr., San Diego, California 92121, United States.

LONP1 is an AAA+ protease that maintains mitochondrial homeostasis by removing damaged or misfolded proteins. Elevated activity and expression of LONP1 promotes cancer cell proliferation and resistance to apoptosis-inducing reagents. Despite the importance of LONP1 in human biology and disease, very few LONP1 inhibitors have been described in the literature. Read More

Mater Sci Eng C Mater Biol Appl 2021 Apr 12;123:111966. Epub 2021 Feb 12.

Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin 300070, China. Electronic address:

Herein, we integrate cell-imprinted substrate (CIS) and allochroic-graphene oxide (AGO) for specific visualization sorting of hepatocellular carcinoma cells. The state-of-the-art-of detection method relies on the enzyme linked immunosorbent assay (ELISA)-like sandwich strategy with hierarchical recognition. The target tumor cells are first selectively captured by the CIS based on cell imprinted recognition, and then specifically labeled with AGO by boronate affinity recognition between boronic acid on AGO and cis-diols on the surface of target cells. Read More

Molecules 2021 Mar 13;26(6). Epub 2021 Mar 13.

Centre of Chemistry, University of Minho, 4710-057 Braga, Portugal.

A series of novel functionalized methyl 3-(hetero)arylthieno[3,2-]pyridine-2-carboxylates - were synthesized by C-C Pd-catalyzed Suzuki-Miyaura cross-coupling of methyl 3-bromothieno[3,2-]pyridine-2-carboxylate with (hetero)aryl pinacol boranes, trifluoro potassium boronate salts or boronic acids. Their antitumoral potential was evaluated in two triple negative breast cancer (TNBC) cell lines-MDA-MB-231 and MDA-MB-468, by sulforhodamine B assay. Their effects on the non-tumorigenic MCF-12A cells were also evaluated. Read More

Biomimetics (Basel) 2021 Mar 15;6(1). Epub 2021 Mar 15.

Department of Chemistry and Biochemistry, University of Hull, Hull HU67RX, UK.

Antimould agents are widely used in different applications, such as specialty paints, building materials, wood preservation and crop protection. However, many antimould agents can be toxic to the environment. This work aims to evaluate the application of copper oxide nanoparticles (CuONPs) surface modified with boronic acid (BA) terminal groups as antimould agents. Read More

Molecules 2021 Mar 2;26(5). Epub 2021 Mar 2.

Coimbra Chemistry Centre, Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal.

A pharmacophore model for inhibitors of 's DNA Gyrase B was developed, using computer-aided drug design. Subsequently, docking studies showed that 2,5(6)-substituted benzimidazole derivatives are promising molecules, as they possess key hydrogen bond donor/acceptor groups for an efficient interaction with this bacterial target. Furthermore, 5(6)-bromo-2-(2-nitrophenyl)-1-benzimidazole, selected as a core molecule, was prepared on a multi-gram scale through condensation of 4-bromo-1,2-diaminobenzene with 2-nitrobenzaldehyde using a sustainable approach. Read More

Molecules 2021 Mar 14;26(6). Epub 2021 Mar 14.

Department of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Read More

ACS Catal 2020 Nov 27;10(21):13075-13083. Epub 2020 Oct 27.

Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

A unified synthetic strategy to access tertiary four-membered carbo/heterocyclic boronic esters is reported. Use of a Cu(I) catalyst in combination with a modified dppbz ligand enables regioselective hydroboration of various trisubstituted benzylidenecyclobutanes and carbo/heterocyclic analogs. The reaction conditions are mild, and the method tolerates a wide range of medicinally relevant heteroarenes. Read More

Sci Adv 2021 Mar 31;7(14). Epub 2021 Mar 31.

School of Biomedical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China.

Excessive carbohydrate intake is linked to the growing prevalence of diabetes, nonalcoholic fatty liver disease (NAFLD), and obesity. α-Glucosidases inhibitor, the only Food and Drug Administration-approved drug for limiting the absorption of polysaccharides and disaccharides, is ineffective for monosaccharides. Here, we develop a boronic acid-containing polymer nanocomplex (Nano-Poly-BA), absorbing all saccharides into nanocomplex with the diol/boronic acid molar ratio far above 1, to prevent saccharides' absorption in the gut. Read More

Inorg Chem 2021 Mar 31. Epub 2021 Mar 31.

Department of Chemistry, College of Chemistry and Chemical Engineering, Ministry of Education (MOE) Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials, Xiamen University, Xiamen 361005, China.

We report a new scheme for chiral recognition using coordination polymers of Ag with a chiral thiol ligand that contains a binding group. -Benzoyl-l-cysteine ethyl ester equipped with a boronic acid group at the para position of the phenyl ring forms coordination polymers with Ag in alkaline aqueous solutions that exhibit excellent selectivity toward a d-glucose enantiomer over l-glucose, while the coordination polymers from the d-cysteine-based thiol ligand are specific for l-glucose. It is assumed that a conformation change occurs upon interaction of a saccharide molecule with the polymeric chain receptor, for which the next binding is promoted, leading to the highly effective chiral recognition, despite the flexible nature of the polymeric receptor. Read More

Cont Lens Anterior Eye 2021 Apr 25;44(2):398-430. Epub 2021 Mar 25.

School of Optometry and Vision Science, UNSW Sydney, Sydney, NSW, Australia.

Contact lenses in the future will likely have functions other than correction of refractive error. Lenses designed to control the development of myopia are already commercially available. Contact lenses as drug delivery devices and powered through advancements in nanotechnology will open up further opportunities for unique uses of contact lenses. Read More

J Org Chem 2021 Apr 26;86(8):5660-5667. Epub 2021 Mar 26.

Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States.

The conjugate addition of aryl boronic acids to enones is a powerful synthetic tool to introduce quaternary chiral centers, but the experimentally observed stereoselectivities vary widely, and the identification of suitable substrate-ligand combinations requires significant effort. We describe the development and application of a transition-state force field (TSFF) by the quantum-guided molecular mechanics (Q2MM) method that is validated using an automated screen of 9 ligands, 38 aryl boronic acids, and 22 enones, leading to a MUE of 1.8 kJ/mol and a value of 0. Read More

Org Lett 2021 Apr 25;23(8):3130-3135. Epub 2021 Mar 25.

Normandy University, University of Rouen, INSA Rouen, CNRS, COBRA UMR 6014, 1 rue Tesnière, 76821 Mont-Saint Aignan Cedex, France.

Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp)-C(sp) allyl coupling has the advantage of using cheap, abundant, and nontoxic CuO without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position. Read More

J Am Chem Soc 2021 Apr 23;143(13):4921-4927. Epub 2021 Mar 23.

Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-8548, United States.

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. Read More

Adv Mater 2021 Mar 22:e2100119. Epub 2021 Mar 22.

School of Chemical and Biological Engineering, Institute of Chemical Processes, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul, 08826, Republic of Korea.

Organic neuromorphic devices and sensors that mimic the functions of chemical synapses and sensory perception in humans have received much attention for next-generation computing and integrated logic circuits. Despite recent advances, organic artificial synapses capable of detecting both neurotransmitters in liquid environments and light are not reported. Herein, inspired by hippocampal synapses, a dual-gate organic synaptic transistor platform with a photoconductive polymer semiconductor, a ferroelectric insulator of P(VDF-TrFE), and an extended-gate electrode functionalized with boronic acid is developed to simultaneously detect the neurotransmitter dopamine and light. Read More