Selective cleavage of 10-methyl benzo[b]naphtho[2,1-d]thiophene by recombinant Mycobacterium sp. strain.
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.
Watanabe
Kimiko
K
Bio-Refining Process Laboratory, Technical Cooperation Department, Japan Cooperation Center, Petroleum, 1900 Sodeshi-cho, Shimizu-shi, Shizuoka 424-0037, Japan. Kiwatanabe@brpl.jccp.or.jp
Noda
Ken-ichi
K
Maruhashi
Kenji
K
D001673:Biodegradation, Environmental; D009161:Mycobacterium / Q000737:chemistry / Q000145:classification / Q000378:metabolism*; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism*; D011995:Recombination, Genetic; D012680:Sensitivity and Specificity; D013045:Species Specificity; D013455:Sulfur / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry / Q000378:metabolism*
C477391:10-methyl benzo(b)naphtho(2,1-d)thiophene; D009281:Naphthalenes; D013876:Thiophenes; D013455:Sulfur; C016366:dibenzothiophene