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β-酮硫醚生物转化制备手性β-羟基亚砜

Biotransformation of beta-ketosulfides to produce chiral beta-hydroxysulfoxides.

作者信息

Holland H L, Brown F M, Barrett F, French J, Johnson D V

机构信息

Department of Chemistry, Brock University, ON L2S 3A1, St. Catharines, Canada.

出版信息

J Ind Microbiol Biotechnol. 2003 May;30(5):292-301. doi: 10.1007/s10295-003-0050-4. Epub 2003 May 21.

DOI:10.1007/s10295-003-0050-4
PMID:12759809
Abstract

The biotransformations of a series of substituted phenylthio-2-propanone and benzylthio-2-propanone were carried out using Helminthosporium sp. NRRL 4671, Mortierella isabellina ATCC 42613, or Rhodococcus erythropolis IGTS8. Several products gave microbial oxidation of sulfide to sulfoxide and reduction of carbonyl to secondary alcohol, producing beta-hydroxysulfoxides in medium to high enantiomeric and diastereomeric purities. Fungal biotransformations using Helminthosporium sp. and M. isabellina resulted in the opposite sulfoxide configurations of various beta-hydroxysulfoxide products.

摘要

使用稻瘟病菌NRRL 4671、深黄被孢霉ATCC 42613或红平红球菌IGTS8对一系列取代苯硫基-2-丙酮和苄硫基-2-丙酮进行生物转化。几种产物使硫化物微生物氧化为亚砜,并使羰基还原为仲醇,以中等至高对映体和非对映体纯度生成β-羟基亚砜。使用稻瘟病菌和深黄被孢霉进行的真菌生物转化导致各种β-羟基亚砜产物的亚砜构型相反。

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