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有机硫化物的生物转化——IV. 蠕孢菌属NRRL 4671菌株催化形成手性苄基烷基和苯基烷基亚砜

Biotransformation of organic sulfides--IV. Formation of chiral benzyl alkyl and phenyl alkyl sulfoxides by Helminthosporium species NRRL 4671.

作者信息

Holland H L, Brown F M, Larsen B G

机构信息

Department of Chemistry, Brock University, St. Catharines, Ontario, Canada.

出版信息

Bioorg Med Chem. 1994 Jul;2(7):647-52. doi: 10.1016/0968-0896(94)85013-5.

DOI:10.1016/0968-0896(94)85013-5
PMID:7858971
Abstract

The fungus Helminthosporium species NRRL 4671 has been used for the biotransformation of a series of phenyl alkyl sulfides with alkyl groups ranging from methyl to n-hexyl, and benzyl alkyl sulfides with alkyl groups from methyl to n-nonyl. Several 2-phenylethyl and 3-phenylpropyl sulfides have also been examined as substrates, together with cyclohexyl methyl sulfide and 1- and 2-naphthyl methyl sulfides. For the majority of substrates, sulfoxide formation occurred in moderate yield and with predominant (S) chirality at sulfur; lesser amounts of sulfone product were also obtained in some cases. The data so obtained have been used to define the preparatively useful limits of S-oxidation of phenyl alkyl sulfides and benzyl alkyl sulfides by biotransformation using Helminthosporium.

摘要

真菌链格孢属NRRL 4671已被用于一系列苯烷基硫化物的生物转化,这些苯烷基硫化物的烷基从甲基到正己基,以及苄基烷基硫化物,其烷基从甲基到正壬基。几种2-苯乙基和3-苯丙基硫化物也作为底物进行了研究,还有环己基甲基硫化物以及1-萘基甲基硫化物和2-萘基甲基硫化物。对于大多数底物,亚砜形成的产率适中,且硫原子处具有主要的(S)手性;在某些情况下也获得了较少量的砜产物。由此获得的数据已用于确定使用链格孢属通过生物转化对苯烷基硫化物和苄基烷基硫化物进行S-氧化的制备有用限度。

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