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Enzymatic Synthesis of Noncanonical α-Amino Acids Containing γ-Tertiary Alcohols

文献类型：期刊论文

作者Zhang, Rui1; Zhang, Chenghua2,7; Tan, Jiamu1,10; He, Yifan3,10; Zhuo, Dan4; Zhang, Jingxuan1,10; Luo, Zhenzhen4; Li, Qiaoqiao4; Yao, Jiaying5,6; Ke, Changqiang3
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2024-01-11
页码9
ISSN号1433-7851
关键词Asymmetric Synthesis Biocatalysis Noncanonical Amino Acids Quantum Chemical Calculations Tertiary Alcohols
DOI10.1002/anie.202318550
通讯作者Zhang, Rui(zhangrui4@simm.ac.cn) ; He, Shijun(heshijun@shutcm.edu.cn) ; Sheng, Xiang(shengx@tib.cas.cn) ; Liao, Cangsong(csliao@Simm.ac.cn)
英文摘要Noncanonical amino acids (ncAAs) containing tertiary alcohols are valuable as precursors of natural products and active pharmaceutical ingredients. However, the assembly of such ncAA scaffolds from simple material by C-C bond formation remains a challenging task due to the presence of multiple stereocenters and large steric hindrance. In this study, we present a novel solution to this problem through highly selective enzymatic decarboxylative aldol addition. This method allows for the streamlined assembly of multifunctionalized ncAAs with gamma-tertiary alcohols from readily available materials, such as L-aspartatic acid and isatins, vicinal diones and keto esters. The modularity of electrophiles furnished four classes of ncAAs with decent efficiency as well as excellent site and stereocontrol. Computational modeling was employed to gain detailed insight into the catalytic mechanism and to provide a rationale for the observed selectivities. The method offers a single-step approach to producing multifunctionalized ncAAs, which can be directly utilized in peptide synthesis and bioactivity assessment. An enzymatic decarboxylative aldol reaction was developed for the synthesis of noncanonical alpha-amino acids containing gamma-tertiary alcohol groups. The modularity of the electrophile enabled access to four classes of ncAAs with high efficiency as well as excellent regioselectivity and stereoselectivity.+image
WOS关键词NONRIBOSOMAL PEPTIDE ; MOLECULAR-DYNAMICS
资助项目National Natural Science Foundation of China[22071259] ; National Natural Science Foundation of China[22103095] ; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, National Natural Science Foundation of China (NSFC)[20PJ1415700] ; Shanghai Pujiang Program[TSBICIP-CXRC-026] ; Tianjin Synthetic Biotechnology Innovation Capacity Improvement Project
WOS研究方向Chemistry
语种英语
出版者WILEY-V C H VERLAG GMBH
WOS记录号WOS:001140218300001
源URL[http://119.78.100.183/handle/2S10ELR8/308672]  
专题中国科学院上海药物研究所
通讯作者Zhang, Rui; He, Shijun; Sheng, Xiang; Liao, Cangsong
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China
2.Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin 300308, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
4.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
5.Jiangxi Univ Chinese Med, Grad Sch, Nanchang 330004, Peoples R China
6.Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Shanghai 201203, Peoples R China
7.North Sichuan Med Coll, Sch Pharm, Nanchong 637100, Peoples R China
8.Natl Ctr Technol Innovat Synthet Biol, Natl Engn Res Ctr Ind Enzymes, Tianjin 300308, Peoples R China
9.Key Lab Engn Biol Low Carbon Mfg, Tianjin 300308, Peoples R China
10.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Zhang, Rui,Zhang, Chenghua,Tan, Jiamu,et al. Enzymatic Synthesis of Noncanonical α-Amino Acids Containing γ-Tertiary Alcohols[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024:9.
APA Zhang, Rui.,Zhang, Chenghua.,Tan, Jiamu.,He, Yifan.,Zhuo, Dan.,...&Liao, Cangsong.(2024).Enzymatic Synthesis of Noncanonical α-Amino Acids Containing γ-Tertiary Alcohols.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,9.
MLA Zhang, Rui,et al."Enzymatic Synthesis of Noncanonical α-Amino Acids Containing γ-Tertiary Alcohols".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2024):9.

入库方式： OAI收割

来源：上海药物研究所

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