MICROBIAL OXIDATION OF BENZYL SULFIDES AND BIBENZYL BY MORTIERELLA-ISABELLINA AND HELMINTHOSPORIUM SPECIES

被引:35
作者
HOLLAND, HL
RAND, CG
VISKI, P
BROWN, FM
机构
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 12期
关键词
BIOTRANSFORMATION; ENZYMES; SULFOXIDES;
D O I
10.1139/v91-287
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The biotransformation of 1,2-diphenylethane by the fungus Mortierella isabellina ATCC 42613, and that of a series of alkyl benzyl sulfides by the fungi M. isabellina and Helminthosporium species NRRL 4671 have been studied. Mortierella hydroxylates 1,2-diphenylethane in low yield, giving (S)-1,2-diphenylethanol with an enantiomeric purity of 33%. Bioconversions of deuterium-labelled and racemic 1,2-diphenylethanol by M. isabellina demonstrate that this organism performs reversible oxidation/reduction of the alcohol. Biotransformations of n-alkyl benzyl sulfides by H. species give predominantly the (S) enantiomer of sulfoxide, with no sulfone formation, but M. isabellina, although showing a general preference for the oxidation of alkyl benzyl sulfides to (R) sulfoxides, also generates sulfones from n-alkyl benzyl sulfides in a time-dependent manner that suggests a stereoselective removal of (R) sulfoxide. The latter microorganism can be used, however, for the production of (R)-benzyl methyl and benzyl isopropyl sulfoxides, and gives (S)-benzyl tert-butyl sulfoxide in low yield.
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页码:1989 / 1993
页数:5
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