ICCAS OpenIR
Nitrile biotransformations for the synthesis of highly enantioenriched beta-hydroxy and beta-amino acid and amide derivatives: A general and simple but powerful and efficient benzyl protection strategy to increase enantioselectivity of the amidase
Ma, Da-You; Wang, De-Xian; Pan, Jie; Huang, Zhi-Tang; Wang, Mei-Xiang
2008-06-06
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume73Issue:11Pages:4087-4091
AbstractBiotransformations of a number of racemic beta-hydroxy and beta-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the Substrates. While biotransformations of beta-hydroxy and beta-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the beta-hydroxy and beta-amino of nitrile substrates led to the formation of highly enantioenriched beta-benzyloxy and beta-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure beta-hydroxy and beta-amino acids.
DOI10.1021/jo800074k
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000256323500012
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:42[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/64340
Collection中国科学院化学研究所
Corresponding AuthorWang, Mei-Xiang
AffiliationChinese Acad Sci, Inst Chem, Biol Chem Lab, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Ma, Da-You,Wang, De-Xian,Pan, Jie,et al. Nitrile biotransformations for the synthesis of highly enantioenriched beta-hydroxy and beta-amino acid and amide derivatives: A general and simple but powerful and efficient benzyl protection strategy to increase enantioselectivity of the amidase[J]. JOURNAL OF ORGANIC CHEMISTRY,2008,73(11):4087-4091.
APA Ma, Da-You,Wang, De-Xian,Pan, Jie,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2008).Nitrile biotransformations for the synthesis of highly enantioenriched beta-hydroxy and beta-amino acid and amide derivatives: A general and simple but powerful and efficient benzyl protection strategy to increase enantioselectivity of the amidase.JOURNAL OF ORGANIC CHEMISTRY,73(11),4087-4091.
MLA Ma, Da-You,et al."Nitrile biotransformations for the synthesis of highly enantioenriched beta-hydroxy and beta-amino acid and amide derivatives: A general and simple but powerful and efficient benzyl protection strategy to increase enantioselectivity of the amidase".JOURNAL OF ORGANIC CHEMISTRY 73.11(2008):4087-4091.
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