Purely Chemical Approach for Preparation of D-alpha-Amino Acids via (S)-to-(R)-Interconversion of Unprotected Tailor-Made alpha-Amino Acids

doi:10.1021/acs.joc.5b02707

	Purely Chemical Approach for Preparation of D-alpha-Amino Acids via (S)-to-(R)-Interconversion of Unprotected Tailor-Made alpha-Amino Acids
	Nian, Yong 2; Wang, Jiang2 ; Zhou, Shengbin 2; Dai, Wenhao 2; Wang, Shuni 2; Moriwaki, Hiroki 3; Kawashima, Aki 3; Soloshonok, Vadim A.1,4; Liu, Hong2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2016-05-06
卷号	81 期号:9 页码:3501-3508
ISSN号	0022-3263
DOI	10.1021/acs.joc.5b02707
文献子类	Article
英文摘要	Unnatural (R)-alpha-amino acids (alpha-AAs) are in growing demand in the biomedical research and pharmaceutical industries. In this work, we present development of a purely chemical approach for preparation of (R)-alpha-AAs via (S)-to-(R)interconversion of natural and tailor-made (S)-alpha-AAs. The method can be used on free, unprotected a-AAs and features a remarkable structural generality including substrates bearing tertiary alkyl chains and reactive functional groups. These attractive characteristics, combined with simplicity of reaction conditions and virtually complete stereochemical outcome, constitute a true methodological advance in this area, rivaling previously reported chemical and biocatalytic approaches.
资助项目	National Natural Science Foundation of China[91229204] ; National Natural Science Foundation of China[81220108025] ; Major Project of Chinese National Programs for Fundamental Research and Development[2015CB910304] ; Shanghai Science and Technology Development Funds[00000000]
WOS关键词	DYNAMIC KINETIC RESOLUTION ; ASYMMETRIC-SYNTHESIS ; STEREOSELECTIVE-SYNTHESIS ; DERIVATIVES ; BIOTRANSFORMATIONS ; DERACEMIZATION ; PEPTIDES ; LIGANDS ; GLYCINE
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000375890100004
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276043]
专题	药物化学研究室
通讯作者	Soloshonok, Vadim A.; Liu, Hong
作者单位	1.Univ Basque Country UPV EHU, Dept Organ Chem 1, Fac Chem, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain; 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 3.Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan; 4.Basque Fdn Sci, Ikerbasque, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain
推荐引用方式 GB/T 7714	Nian, Yong,Wang, Jiang,Zhou, Shengbin,et al. Purely Chemical Approach for Preparation of D-alpha-Amino Acids via (S)-to-(R)-Interconversion of Unprotected Tailor-Made alpha-Amino Acids[J]. JOURNAL OF ORGANIC CHEMISTRY,2016,81(9):3501-3508.
APA	Nian, Yong.,Wang, Jiang.,Zhou, Shengbin.,Dai, Wenhao.,Wang, Shuni.,...&Liu, Hong.(2016).Purely Chemical Approach for Preparation of D-alpha-Amino Acids via (S)-to-(R)-Interconversion of Unprotected Tailor-Made alpha-Amino Acids.JOURNAL OF ORGANIC CHEMISTRY,81(9),3501-3508.
MLA	Nian, Yong,et al."Purely Chemical Approach for Preparation of D-alpha-Amino Acids via (S)-to-(R)-Interconversion of Unprotected Tailor-Made alpha-Amino Acids".JOURNAL OF ORGANIC CHEMISTRY 81.9(2016):3501-3508.