Optically active chlorohydrins as chiral C3 and C4 building units: Microbial resolution and synthetic applications

来自 Wiley

阅读量:

36

作者:

NaoyaKasaiToshioSuzukiandYoshiroFurukawa

展开

摘要:

Production of highly optically active C3 and C4 chlorohydrins was developed by using the bacteria stereoselectively dehalogenating and assimilating the racemic substrate: Pseudomonas sp. and Alcaligenes sp. These bacteria stereoselectively assimilate (RS)-2,3-dichloro-1-propanol (DCP) and (RS)-3-chloro-1,2-propanediol (CPD) followed by microbial preparation of (R)- and (S)-DCP, and (R)- and (S)-CPD with >99% ee. A novel dehalogenating enzyme, halohydrin dehydro-dehalogenase from one of the above strains, Alcaligenes sp. DS-S-7G, was applicable for preparation of optically active 1,2-diols with 60–99% ee. Moreover, microbial resolution of C4 chlorohydrins with whole cells of Pseudomonas sp. was carried out. This resolution reaction using the resting cells gave (R)- and (S)-4-chloro-3-hydroxybutyrate (CHB) and (S)-4-chloro-3-hydroxybutyronitrile (BN) with >98% ee. In the case of the resting cells of Enterobacter sp., both (R)-CHB (>99% ee) and (S)-3-hydroxy--butyrolactone (95% ee) with excellent yield were obtained. Also, some typical synthetic applications using the above chiral C3 and C4 synthons were introduced: ferroelectric liquid crystals, optically active β-blockers, and other chiral pharmaceuticals. Chirality 10:682–692, 1998. © 1998 Wiley-Liss, Inc.

展开

DOI:

10.1002/(SICI)1520-636X(1998)10:7<682::AID-CHIR14>3.0.CO;2

被引量:

25

年份:

1998

通过文献互助平台发起求助,成功后即可免费获取论文全文。

相似文献

参考文献

引证文献

来源期刊

研究点推荐

引用走势

2013
被引量:5

站内活动

辅助模式

0

引用

文献可以批量引用啦~
欢迎点我试用!

关于我们

百度学术集成海量学术资源,融合人工智能、深度学习、大数据分析等技术,为科研工作者提供全面快捷的学术服务。在这里我们保持学习的态度,不忘初心,砥砺前行。
了解更多>>

友情链接

百度云百度翻译

联系我们

合作与服务

期刊合作 图书馆合作 下载产品手册

©2025 Baidu 百度学术声明 使用百度前必读

引用