重组分枝杆菌菌株对10-甲基苯并[b]萘并[2,1-d]噻吩的选择性裂解

Selective cleavage of 10-methyl benzo[b]naphtho[2,1-d]thiophene by recombinant Mycobacterium sp. strain.

作者信息

Watanabe Kimiko, Noda Ken-ichi, Maruhashi Kenji

机构信息

Bio-Refining Process Laboratory, Technical Cooperation Department, Japan Cooperation Center, Petroleum, 1900 Sodeshi-cho, Shimizu-shi, Shizuoka 424-0037, Japan.

出版信息

Biotechnol Lett. 2003 May;25(10):797-803. doi: 10.1023/a:1023584805911.

DOI:10.1023/a:1023584805911

PMID:12882010

Abstract

Recombinant Mycobacterium sp. strain MR65 carrying dszABCD genes was used for desulfurization of 10-methylbenzo[b]naphtho[2,1-d]thiophene (10-methyl BNT) in the hexadecane phase. The specific activity was 25% of that of dibenzothiophene (DBT). One of two major metabolites of 10-methyl BNT produced by strain MR65 was identified as 1-methoxy-2-(3-methylphenyl)naphthalene by 1H and 13C NMR. The other major metabolite and two minor metabolites were determined as 1-hydroxy-2-(3-methylphenyl)naphthalene, 2-(2-methoxy-3-methylphenyl)naphthalene and 2-(2-hydroxy-3-methylphenyl)naphthalene, respectively, by HPLC and GC-MS. The production ratio of the two desulfurization metabolite isomers was 0.99:0.01, calculated on the basis of peak GC areas. These results indicated that the C-S bond adjacent to the naphthalene skeleton was selectively cleaved to form the two major compounds.

摘要

携带dszABCD基因的重组分枝杆菌菌株MR65用于十六烷相中10-甲基苯并[b]萘并[2,1-d]噻吩（10-甲基BNT）的脱硫。比活性为二苯并噻吩（DBT）的25%。菌株MR65产生的10-甲基BNT的两种主要代谢产物之一通过1H和13C NMR鉴定为1-甲氧基-2-（3-甲基苯基）萘。通过HPLC和GC-MS分别将另一种主要代谢产物和两种次要代谢产物确定为1-羟基-2-（3-甲基苯基）萘、2-（2-甲氧基-3-甲基苯基）萘和2-（2-羟基-3-甲基苯基）萘。基于GC峰面积计算，两种脱硫代谢产物异构体的生成比例为0.99:0.01。这些结果表明，与萘骨架相邻的C-S键被选择性裂解，形成了两种主要化合物。