ICCAS OpenIR
Nitrile biotransformations for highly efficient and enantioselective syntheses of electrophilic oxiranecarboxamides
Wang, MX; Lin, SJ; Liu, CS; Zheng, QY; Li, JS
2003-05-30
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume68Issue:11Pages:4570-4573
AbstractCatalyzed by a nitrile hydratase/amidase-containing microbial Rhodococcus sp. AJ270 whole-cell catalyst, a number of racemic trans-2,3-epoxy-3-arylpropanenitriles 1 underwent rapid and efficient hydrolysis under very mild conditions to afford 2R,3S-2-arylglycidamides 2 in excellent yield with enantiomeric excess higher than 99.5%. The overall enantioselectivity of the biotransformations originated from the combined effects of a dominantly high 2S-enantioselective amidase and low 2S-enantioselective nitrile hydratase involved in the cell. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects.
DOI10.1021/jo0267201
Indexed BySCI ; CCR
Language英语
WOS IDWOS:000183066100064
PublisherAMER CHEMICAL SOC
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Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/80662
Collection中国科学院化学研究所
Corresponding AuthorWang, MX
AffiliationChinese Acad Sci, Biol Chem Lab, Ctr Mol Sci, Inst Chem, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Wang, MX,Lin, SJ,Liu, CS,et al. Nitrile biotransformations for highly efficient and enantioselective syntheses of electrophilic oxiranecarboxamides[J]. JOURNAL OF ORGANIC CHEMISTRY,2003,68(11):4570-4573.
APA Wang, MX,Lin, SJ,Liu, CS,Zheng, QY,&Li, JS.(2003).Nitrile biotransformations for highly efficient and enantioselective syntheses of electrophilic oxiranecarboxamides.JOURNAL OF ORGANIC CHEMISTRY,68(11),4570-4573.
MLA Wang, MX,et al."Nitrile biotransformations for highly efficient and enantioselective syntheses of electrophilic oxiranecarboxamides".JOURNAL OF ORGANIC CHEMISTRY 68.11(2003):4570-4573.
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