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Divergent synthesis of chiral amines via Ni-catalyzed chemo-and enantioselective hydrogenation of alkynone imines

Science China Chemistry 2023年第11期66卷 3186-3192页

作者： Yuchuan Ma Kai Liu Lin He Hui Lv Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan School of Chemistry and Chemical EngineeringShihezi UniversityShihezi 832000China Hubei Key Lab on Organic and Polymeric Optoelectronic Materials Engineering Research Center of Organosilicon Compounds&MaterialsMinistry of EducationSauvage Center for Molecular SciencesKey Laboratory of Biomedical Polymers of Ministry of Education&College of Chemistry and Molecular SciencesWuhan UniversityWuhan 430072China

Ligand-mediated nickel-catalyzed asymmetric hydrogenation of alkynone imines has been achieved. By using Ni(OAc)_2·4H_2O/(S,S)-Ph-BPE complex as a catalyst, the chemo-and enantioselective hydrogenation of alkynone imines occurred efficiently to afford chiral propargyl amines with high yields and excellent enantioselectivities(up to 99% yield, >99% ee), leaving the readily reducible alkynyl group intact. Both the C=N and C≡C bonds of alkynone imines were hydrogenated efficiently in the presence of Ni(OAc)_2·4H_2O and Josiphos SL-J011-1, furnishing unfunctionalized chiral imines efficiently(up to 99% yield, >99% ee).The(Z)-allylamines and(E)-allylamines were also efficiently prepared from alkynone imines by the combination of the different catalytic systems. The preliminary mechanism study revealed that the reduction of alkynone imines was a stepwise process and the C=N bonds were preferably hydrogenated in the complete reduction of alkynone imines. The synthetic utility of this method was demonstrated by its application in the late-stage modification of the antiviral drug Zidovudine and the concise synthesis of chiral dibenzoazepine.

关键词： alkynone imine asymmetric hydrogenation propargyl amine enantioselectivity chiral amine

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Multifunctional biocatalysis:An unusual imine reductase

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Engineering Microbiology 2022年第2期2卷 42-44页

作者： Feifei Chen Jianhe Xu Gaowei Zheng State Key Laboratory of Bioreactor Engineering Shanghai Collaborative Innovation Center for BiomanufacturingEast China University of Science and TechnologyShanghai 200237China

A multifunctional biocatalyst EneIRED capable of catalyzing amine-activated conjugate alkene reduction and subsequent reductive amination was discovered.The enzyme realized the coupling ofα,β-unsaturated carbonyls with amines to efficiently synthesize a broad set of chiral amine diastereomers based on its unusual active site structure and catalytic mechanism.

关键词： Imine reductase Biocatalysis chiral amine Conjugate reduction Reductive amination

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Mining of aminotransferase gene ota3 from Bacillus pumilus W3 via genome analysis,gene cloning and expressing for compound bioamination

Mining of aminotransferase gene ota3 from Bacillus pumilus W...

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华东六省一市生物化学与分子生物学会联盟2019年学术与...

作者： Lixin Zhai Shaolan Yang Di Meng Qiaopeng Tian Xiangru Liao Key Laboratory of Industrial Biotechnology Ministry of EducationSchool of BiotechnologyJiangnan University

Aminotransferases are widely employed as biocatalysts to produce chiral amines and biologically active pharmaceuticals via asymmetric synthesis.The complete Bacillus pumilus W3 genome is available from NCBI(National Center for Biotechnology Information).One hypothetical protein co-BPTA as pyridoxal 5’-phosphate dependent enzymes class Ⅳ(PLPDE;aminotransferase class Ⅳ) was chosen from Bacillus pumilus W3,The sequence of ota3 shares highest sequence identity(24.7%) with the first(R)-selective aminotransferase from Arthrobacter sp.KNK 168.Both native and codon-optimised ω-BPAT genes were recombinantly expressed,and the purified proteins had a molecular mass of ～33.4 kDa.Moreover,the relationships between comprehensive performance of ω-BPTA(activity and stability) and reaction conditions(pH and temperature) were investigated by carrying out a single-variable test with phenethylamine and pyruvate as donor and acceptor respectively.Enantioselectivity tests with(S)-and(R)-a-phenethylamine revealed its(R)-selectivity.The optimal conditions for catalytic reaction were 45℃ and pH 7.0,and ω-BPAT retained stability at 20℃ and pH 7.0.Thus,co-BPAT is a novel(R)-selective aminotransferase with great potential as a universal biocatalyst.This method provided an approach for the rapid screening of transaminases,and a reference for future rational engineering of co-BPTA to improve substrate specificity and conversion efficiency.

关键词： Aminotransferase Genome analysis Bioinformatics chiral amine Bacillus pumilus W3

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