2,274 results match your criteria resolution racemic

Photoinduced Reversible Semicrystalline-to-Amorphous State Transitions of Stereoregular Azopolyesters.

Angew Chem Int Ed Engl 2021 Jun 15. Epub 2021 Jun 15.

Dalian University of Technology, State Key Laboratory of Fine Chemicals, CHINA.

Precise control over both the chirality and sequence of a synthetic polymer is critical for manipulating its material performance. Herein, we report the synthesis of a variety of isotactic azobenzene-based polyesters (azopolyesters) with main-chain chirality via highly enantioselective resolution copolymerization of racemic azobenzene-containing epoxides with cyclic anhydrides, using an enantiopure binuclear catalyst system. All the prepared polyesters bearing trans -azobenzene moieties were found to be typical semicrystalline materials with melting temperatures in the range of 153 to 231 °C, while the corresponding isotactic cis -azopolyesters were amorphous. Read More

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Finite-temperature effect in the O-acylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B.

J Mol Graph Model 2021 May 31;107:107951. Epub 2021 May 31.

Grupo de Bioquímica Teórica, Universidad Industrial de Santander, Cra 27 Calle 9, Bucaramanga, Colombia. Electronic address:

CalB is a triacylglycerol hydrolase (E.C.3. Read More

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Alkyl-benzofuran dimers from Eupatorium chinense with insulin-sensitizing and anti-inflammatory activities.

Bioorg Chem 2021 Aug 27;113:105030. Epub 2021 May 27.

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, People's Republic of China; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, People's Republic of China. Electronic address:

Five new racemic alkyl-benzofuran dimers, (±)-dieupachinins I-M (1-5), were isolated from the root tubers of Eupatorium chinense, a well-known traditional Chinese medicine for the treatment of diphtheria in Guangdong province. The structures of these compounds, especially the first examples of 12,10'-epoxy dimer dieupachinin I (1), 12-nor-dimer dieupachinin J (2), and 12,12'-dinor-dimer dieupachinin K (3), were elucidated by spectroscopic data analysis. Chiral resolution were further carried out on a cellulose column by HPLC, and compounds 2-5 were successfully separated into two enantiomers, respectively. Read More

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Enantioselective α-Etherification of Branched Aldehydes via an Oxidative Umpolung Strategy.

Angew Chem Int Ed Engl 2021 Jun 4. Epub 2021 Jun 4.

Aarhus University, Chemistry, Langelandsgade 140, 800, Aarhus, DENMARK.

Saturated carbonyl compounds are, via their enolate analogs, inherently nucleophilic at the α-position. In the presence of a benzoquinone oxidant, the polarity of the α-position of racemic α-branched aldehydes is inverted, allowing for an enantioselective etherification using readily available oxygen-based nucleophiles and an amino acid-derived primary amine catalyst. A survey of benzoquinone oxidants identified p -fluoranil and DDQ as suitable reaction partners. Read More

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Prebiotic access to enantioenriched glyceraldehyde mediated by peptides.

Chem Sci 2021 Mar 31;12(18):6350-6354. Epub 2021 Mar 31.

Department of Chemistry, Scripps Research La Jolla CA 92037 USA

A prebiotically plausible route to enantioenriched glyceraldehyde is reported a kinetic resolution mediated by peptides. The reaction proceeds a selective reaction between the l-peptide and the l-sugar producing an Amadori rearrangement byproduct and leaving d-glyceraldehyde in excess. Solubility considerations in the synthesis of proline-valine (pro-val) peptides allow nearly enantiopure pro-val to be formed starting from racemic pro and nearly racemic (10%) ee val. Read More

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Chiral Nanochannels of Ordered Mesoporous Silica Constructed by a Pillar[5]arene-Based Host-Guest System.

ACS Appl Mater Interfaces 2021 Jun 2;13(23):27305-27312. Epub 2021 Jun 2.

Key Laboratory of Pesticide and Chemical Biology (CCNU), Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.

The separation of racemic compounds by chiral nanochannels has attracted extensive attention. However, the fabrication of high-performance chiral nanochannels is still a challenge owing to the difficulty in magnifying the weak chiral interaction to macroscopic properties of materials. Herein, by introducing a l-alanine-pillar[5]arene host to achiral ordered mesoporous silica (OMS), chiral OMS nanochannels were fabricated, which exhibited excellent selectivity (ee value up to 90. Read More

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Simple Plug-In Synthetic Step for the Synthesis of (-)-Camphor from Renewable Starting Materials.

Chembiochem 2021 May 25. Epub 2021 May 25.

Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, 8010, Graz, Austria.

Racemic camphor and isoborneol are readily available as industrial side products, whereas (1R)-camphor is available from natural sources. Optically pure (1S)-camphor, however, is much more difficult to obtain. The synthesis of racemic camphor from α-pinene proceeds via an intermediary racemic isobornyl ester, which is then hydrolyzed and oxidized to give camphor. Read More

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Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution.

Org Lett 2021 Jun 17;23(11):4332-4336. Epub 2021 May 17.

Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.

The stereocontrol of tertiary alcohols represents a recurrent challenge in organic synthesis. In the present paper, we describe a simple, efficient, and indirect method to enantioselectively prepare tertiary alcohols through a chiral isothiourea catalyzed selective acylation of adjacent secondary alcohols. This transformation enables the kinetic resolution (KR) of easily prepared racemic diastereoenriched secondary/tertiary diols providing both monoesters and starting diols in highly enantioenriched forms (-value >200). Read More

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Unexpected effects of mobile phase solvents and additives on retention and resolution of N-acyl-D,L-leucine applying Cinchonane-based chiral ion exchangers.

J Chromatogr A 2021 Jul 1;1648:462212. Epub 2021 May 1.

Department of Analytical Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria. Electronic address:

Chiral ion exchangers based on quinine (QN) and quinidine (QD), namely Chiralpak QN-AX and QD-AX as anionic and ZWIX(+) and ZWIX(-) as zwitterionic ion exchanger chiral stationary phases (CSPs) have been investigated with respect to their retention and chiral resolution characteristics. For the evaluation of the effects of the composition of the polar organic bulk solvents of the mobile phase (MP) and those of the organic acid and base additives acting as displacers necessary for a liquid chromatographic ion-exchange process, racemic N-(3,5-dinitrobenzoyl)leucine and other related analytes were applied. The main aim was to evaluate the impact of the MP variations on the observed, and thus the apparent enantioselectivity (α), and the retention factor. Read More

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Mechanistic Insight into the Origin of Stereoselectivity in the Ribose-Mediated Strecker Synthesis of Alanine.

J Am Chem Soc 2021 May 12;143(20):7852-7858. Epub 2021 May 12.

Department of Chemistry, Scripps Research, La Jolla, California 92037, United States.

Enantioenriched amino acids are produced in a hydrolytic kinetic resolution of racemic aminonitriles mediated by chiral pentose sugars. Experimental kinetic and spectroscopic results combined with DFT computational studies and microkinetic modeling help to identify the nature of the intermediate species and provide insight into the stereoselectivity of their hydrolysis in the prebiotically relevant ribose-alanine system. These studies support a synergistic role for sugars and amino acids in the emergence of homochirality in biological molecules. Read More

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Immobilization of cellulase on monolith supported with Zr(IV)-based metal-organic framework as chiral stationary phase for enantioseparation of five basic drugs in capillary electrochromatography.

Mikrochim Acta 2021 May 12;188(6):186. Epub 2021 May 12.

Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, No.24 Tongjiaxiang, Nanjing, Jiangsu, 210009, People's Republic of China.

Metal-organic framework (UiO-66-NH)-incorporated organic polymer monolith was prepared by thermal polymerization. By virtue of the superior physical and chemical properties, the UiO-66-NH-modified organic monolith was then functionalized by chiral selector cellulase via the condensation reaction between the primary amino groups and aldehyde groups. The synthesized materials were characterized by Fourier transform infrared spectroscopy, high-resolution transmission electron microscopy, scanning electron microscopy, X-ray photoelectron spectrometry, thermogravimetric analysis, and nitrogen sorption isotherm. Read More

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Kinetic resolution of indolines by asymmetric hydroxylamine formation.

Nat Commun 2021 05 4;12(1):2512. Epub 2021 May 4.

School of Chemistry and Chemical Engineering, Shandong University, Jinan, China.

Catalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N-O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with environmentally benign hydrogen peroxide as oxidant is applicable to a range of racemic indolines with multiple stereocenters and diverse substituent patterns in high efficiency with efficient chemoselectivity and enantio-discrimination. Read More

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An Asymmetric S2 Dynamic Kinetic Resolution.

J Am Chem Soc 2021 May 4;143(19):7509-7520. Epub 2021 May 4.

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.

The S2 reaction exhibits the classic Walden inversion, indicative of the stereospecific backside attack of the nucleophile on the stereogenic center. Observation of the inversion of the stereocenter provides evidence for an S2-type displacement. However, this maxim is contingent on substitution proceeding on a discrete stereocenter. Read More

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Preparation of (R)-3-aminopiperidine by resolution with optically active cyclic phosphoric acids.

Chirality 2021 07 3;33(7):379-384. Epub 2021 May 3.

College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang, China.

(R)-3-aminopiperidine ((R)-APD), a key intermediate for alogliptin, trelagliptin, and linagliptin, was successfully resolved from racemic 3-aminopiperidine with an enantiomerically pure resolving agent, namely, (R)-4-(2-chlohydroxy-1.3.2-dioxaphosphorinane 2-oxide ((R)-CPA), via diastereomeric salt formation. Read More

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Enantioselective Mixed Matrix Membranes for Chiral Resolution.

Membranes (Basel) 2021 Apr 10;11(4). Epub 2021 Apr 10.

Department of Chemical and Molecular Engineering (BK-21 Plus), Korea Advanced Institute of Science and Technology, Daejeon 34141, Korea.

Most pharmaceuticals are stereoisomers that each enantiomer shows dramatically different biological activity. Therefore, the production of optically pure chemicals through sustainable and energy-efficient technology is one of the main objectives in the pharmaceutical industry. Membrane-based separation is a continuous process performed on a large scale that uses far less energy than the conventional thermal separation process. Read More

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Chemical Constituents of the Egg Cases of (Mantidis ootheca) with Intracellular Reactive Oxygen Species Scavenging Activity.

Biomolecules 2021 Apr 10;11(4). Epub 2021 Apr 10.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine (KIOM), Naju 58245, Korea.

As a traditional medicine with potential antioxidant effects, egg cases (Mantidis ootheca) are a potential source of new bioactive substances. Herein, three new -acetyldopamine derivatives, namely, (+)-tenoderin A (), (-)-tenoderin A (), and tenoderin B (), along with thirteen known compounds (-), were isolated from a 70% EtOH extract of . egg cases. Read More

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Chirality Remote Control in Nanoporous Materials by Circularly Polarized Light.

J Am Chem Soc 2021 May 29;143(18):7059-7068. Epub 2021 Apr 29.

Institute of Functional Interfaces (IFG), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.

The ability to dynamically control chirality remains a grand challenge in chemistry. Although many molecules possess chiral isomers, lacking their isolation, for instance during photoisomerization, results in racemic mixtures with suppressed enantiospecific chiral properties. Here, we present a nanoporous solid in which chirality and enantioselective enrichment is induced by circularly polarized light (CPL). Read More

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Role of the Auxiliary Ligand in the Spontaneous Resolution of Enantiomers in Three-Dimensional Coordination Polymers.

Inorg Chem 2021 May 29;60(10):6981-6985. Epub 2021 Apr 29.

State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

Four pairs of chiral 3D coordination polymers (CPs), [Zn(BDC)(lac)(DMF)]·guest () (HBDC = benzene dicarboxylic acid; Hlac = lactic acid; guest = 1.5DMF + -PrOH), [Co(BDC)(lac)(DMF)]·guest () (guest = DMF + 2HO), [Fe(BDC)(lac)(DMF)](CO)·guest () (guest = DMF + 2HO), and {Zn(BPDC)(lac)[NH(CH)]}·guest (HBPDC = 3,3'-biphenyldicarboxylic acid; guest = 6DMF + 18HO) (), are prepared through the reactions of racemic lactic acid (-Hlac) with different metal ions and auxiliary ligands. Structural analyses and DFT calculations reveal that forming more and stronger coordination bonds between the auxiliary ligand and metal ions is more conducive to the spontaneous resolution of enantiomers in 3D CPs than simply increasing the entropy of the auxiliary ligand itself. Read More

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Multigram-scale HPLC enantioseparation as a rescue pathway for circumventing racemization problem during enantioselective synthesis of ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate.

Chirality 2021 07 27;33(7):324-336. Epub 2021 Apr 27.

LCPM, CNRS, Université de Lorraine, F-54000 Nancy, France.

Racemic ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate is a key synthon for the design of promising therapeutic drugs. It is mainly synthesized from racemic ethyl 2,3-dibromopropionate and 2-aminophenol in presence of K CO in refluxed acetone. Unfortunately, synthesis of (R)- and (S)-enantiomers using the enantioselective version of this reaction, which should normally be performed with a double S 2 mechanism, is unsuitable due to a racemization process involving the dehydrobromination of enantiopure ethyl 2,3-dibromopropionate into ethyl 2-bromoacrylate. Read More

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Backbone-Modified -Symmetrical Chiral Bisphosphine TMS-QuinoxP*: Asymmetric Borylation of Racemic Allyl Electrophiles.

J Am Chem Soc 2021 May 23;143(17):6413-6422. Epub 2021 Apr 23.

Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.

A new -symmetrical -chirogenic bisphosphine ligand with silyl substituents on the ligand backbone, (,)-5,8-TMS-QuinoxP*, has been developed. This ligand showed higher reactivity and enantioselectivity for the direct enantioconvergent borylation of cyclic allyl electrophiles than its parent ligand, (,)-QuinoxP* (e.g. Read More

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Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane.

Beilstein J Org Chem 2021 8;17:800-804. Epub 2021 Apr 8.

Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria.

We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful -factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner. Read More

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Single-Handed Double Helix and Spiral Platelet Formed by Racemate of Dissymmetric Cages.

Angew Chem Int Ed Engl 2021 Jun 26;60(27):15080-15086. Epub 2021 May 26.

Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.

Spontaneous deracemization has been used to separate homochiral domains from the racemic system. However, homochirality can only be referred to when the scales of these domains and systems are specified. To clarify this, we report self-assembly of racemates of dissymmetric cages DC-1 with a cone-shape propeller geometry, forming a centrosymmetric columnar crystalline phase (racemic at crystallographic level). Read More

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Phosphonates enantiomers receiving with fungal enzymatic systems.

Microb Cell Fact 2021 Apr 7;20(1):81. Epub 2021 Apr 7.

Department of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and Technology, Wrocław, Poland.

Background: Phosphonates derivatives are in the area of interests because of their unique chemical-physical features. These compounds manifest variety of biological interactions within the sensitive living cells, including impact on particular enzymes activities. Biological "cause and effect" interactions are based upon the specific matching between the structures and/or compounds and this is usually the result of proper optical configurations of particular chiral moieties. Read More

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Racemic Tartrate/Malate Anions Combine with Racemic Complex Cations to Form Optically Active Ionic Crystals.

Chemistry 2021 Jun 13;27(32):8358-8364. Epub 2021 May 13.

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, 560-0043, Japan.

Spontaneous resolution has attracted continuing attention in various research fields since Pasteur's work on the crystallization behavior of racemic tartrate. Here, a unique example of this phenomenon is reported, involving ionic crystals generated from racemic RR/SS- tartrate or R/S-malate and racemic ΔΔ/ΛΛ-[Ag Rh (2-aminoethanethiolato) ] (ΔΔ/ΛΛ-[1] ) in water. RR- and SS-tartrate selectively recognize the ΛΛ and ΔΔ isomers of [1] to produce ionic crystals of (ΛΛ-[1]) (RR-tartrate) and (ΔΔ-[1]) (SS-tartrate) , respectively, which can undergo spontaneous resolution. Read More

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Structure-guided improvement in the enantioselectivity of an Aspergillus usamii epoxide hydrolase for the gram-scale kinetic resolution of ortho-trifluoromethyl styrene oxide.

Enzyme Microb Technol 2021 May 19;146:109778. Epub 2021 Mar 19.

Wuxi School of Medicine, Jiangnan University, Wuxi, 214122, PR China. Electronic address:

Microtuning the substrate-binding pocket (SBP) of EHs has emerged as an effective approach to manipulate their enantio- or regio-selectivities and activities towards target substrates. Here, the enantioselectivity (enantiomeric ratio, E) of AuEH2 towards a racemic (rac-) ortho-trifluoromethyl styrene oxide (o-TFMSO) was improved via microtuning its SBP. Based on the analysis on the crystal structure of AuEH2, its specific residues I192, Y216, R322 and L344 lining the SBP in close to the catalytic triad were identified for site-saturation mutagenesis. Read More

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Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining.

Org Lett 2021 04 2;23(8):3043-3047. Epub 2021 Apr 2.

The Key Laboratory of Industrial Biotechnology, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. China.

A new bacterial carboxylesterase (CarEst3) was identified by genome mining and found to efficiently hydrolyze racemic methyl 3-cyclohexene-1-carboxylate (-CHCM) with a nearly symmetric structure for the synthesis of ()-CHCM. CarEst3 displayed a high substrate tolerance and a stable catalytic performance. The enantioselective hydrolysis of 4. Read More

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Kinetic Resolution of Tertiary Benzyl Alcohols via Palladium/Chiral Norbornene Cooperative Catalysis.

Angew Chem Int Ed Engl 2021 Jun 6;60(23):12824-12828. Epub 2021 May 6.

Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, Wuhan, 430072, China.

Herein we report a highly enantioselective kinetic resolution of tertiary benzyl alcohols via palladium/chiral norbornene cooperative catalysis. With simple aryl iodides as the resolution reagent, a wide range of readily available racemic tertiary benzyl alcohols are applicable to this method. Both chiral tertiary benzyl alcohols and benzo[c]chromene products are obtained in good to excellent enantioselectivities (selectivity factor up to 544). Read More

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Chirogenesis and Amplification of Molecular Chirality Using Optical Vortices.

Angew Chem Int Ed Engl 2021 Jun 1;60(23):12819-12823. Epub 2021 May 1.

Molecular Chirality Research Center, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.

The study of chirogenesis of organic molecules is important to elucidate the origin of the homochirality of biomolecules on Earth. Here, we have accomplished chiral symmetry breaking from a racemate using optical vortices with orbital angular momentum and a helical wavefront. We propose a new methodology of asymmetric transformation by the combination of enantioselective crystal nucleation by irradiation with optical vortices and crystallization-induced dynamic optical resolution of conglomerate crystals. Read More

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Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution.

Org Lett 2021 04 29;23(8):3070-3075. Epub 2021 Mar 29.

Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan.

A highly efficient dynamic kinetic resolution of cyclic halohydrins was achieved by the asymmetric transfer hydrogenation of racemic α-haloketones. Bifunctional oxo-tethered Ru(II) catalysts could promote the reduction without deterioration of halogens. By structural tuning of the catalyst, chiral alcohols having halogen, ester, carboxamide, and sulfone functions were obtained variably with excellent diastereo- and enantioselectivities (up to >99:1 d. Read More

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Pyrrolyl 4-quinolone alkaloids from the mangrove endophytic fungus Penicillium steckii SCSIO 41025: Chiral resolution, configurational assignment, and enzyme inhibitory activities.

Phytochemistry 2021 Jun 16;186:112730. Epub 2021 Mar 16.

CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, PR China; Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning, 530200, PR China; Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou, 511458, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China. Electronic address:

Six undescribed 4-quinolone alkaloids, including four racemic mixtures, (±)-oxypenicinolines A-D, and two related ones, penicinolines F and G, together with seven known analogues, were isolated from the mangrove-derived fungus Penicillium steckii SCSIO 41025 (Trichocomaceae). The racemates were separated by HPLC using chiral columns. Their structures including absolute configurations were elucidated by extensive spectroscopic analysis, electronic circular dichroism (ECD) experiments, and single-crystal X-ray diffraction analysis. Read More

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