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Asymmetric C1 Extension of Aldehydes through Biocatalytic Cascades for Stereodivergent Synthesis of Mandelic Acids

文献类型：期刊论文

作者Liu, Yanqiong3,4; Fu, Zunyun2; Dong, Haihong3; Zhang, Jingxuan1,3; Mao, Yingle3; Zheng, Mingyue1,2,4; Liao, Cangsong1,3,4
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2023-05-08
卷号62期号:20
关键词Asymmetric C-1 Extension Biocatalysis Biocatalytic Cascades (S)-4-Hydroxymandelate Synthase Mandelic Acids
DOI10.1002/anie.202300906
文献子类Article
英文摘要The development of mild, efficient, and enantioselective methods for preparing chiral building blocks from simple, renewable carbon units has been a long-term goal of the sustainable chemical industry. Mandelate derivatives are valuable pharmaceutical intermediates and chiral resolving agents, but their manufacture relies heavily on highly toxic cyanide. Herein, we report (S)-4-hydroxymandelate synthase (HmaS)-centered biocatalytic cascades for the synthesis of mandelates from benzaldehydes and glycine. We show that HmaS can be engineered to perform R-selective hydroxylation by single-point mutation, empowering the stereodivergent synthesis of both (S)- and (R)-mandelate derivatives. These biocatalytic cascades enabled the production of various mandelate derivatives with high atom economy as well as excellent yields (up to 98 %) and ee values (up to >99 %). This methodology offers an effective cyanide-free technology for greener and sustainable production of mandelate derivatives.
WOS关键词BIOSYNTHESIS ; PATHWAY ; STYRENE ; ROUTES
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000969546500001
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/309643]  
专题新药研究国家重点实验室
通讯作者Mao, Yingle; Zheng, Mingyue; Liao, Cangsong
作者单位1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, State Key Lab Drug Res, Shanghai 201203, Peoples R China;
3.Chinese Acad Sci, Shanghai Inst Mat Med, Chem Biol Res Ctr, Shanghai 201203, Peoples R China;
4.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China;
推荐引用方式
GB/T 7714		 Liu, Yanqiong,Fu, Zunyun,Dong, Haihong,et al. Asymmetric C1 Extension of Aldehydes through Biocatalytic Cascades for Stereodivergent Synthesis of Mandelic Acids[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(20).
APA Liu, Yanqiong.,Fu, Zunyun.,Dong, Haihong.,Zhang, Jingxuan.,Mao, Yingle.,...&Liao, Cangsong.(2023).Asymmetric C1 Extension of Aldehydes through Biocatalytic Cascades for Stereodivergent Synthesis of Mandelic Acids.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(20).
MLA Liu, Yanqiong,et al."Asymmetric C1 Extension of Aldehydes through Biocatalytic Cascades for Stereodivergent Synthesis of Mandelic Acids".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.20(2023).

入库方式： OAI收割

来源：上海药物研究所

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