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Microbial Asymmetric CH Oxidations of Simple Hydrocarbons: A Novel Monooxygenase Activity of the Topsoil Microorganism Bacillus megaterium
Author(s) -
Adam Waldemar,
Lukacs Zoltan,
SahaMöller Chantu R.,
Weckerle Bernhard,
Schreier Peter
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200008)2000:16<2923::aid-ejoc2923>3.0.co;2-l
Subject(s) - bacillus megaterium , chemistry , cyclooctane , monooxygenase , alkane , enantiomeric excess , organic chemistry , substrate (aquarium) , cyclohexane , enantioselective synthesis , bacteria , hydrocarbon , enzyme , cytochrome p450 , ecology , catalysis , genetics , biology
A Bacillus megaterium strain was isolated from topsoil by a selective screening procedure with allylbenzene as xenobiotic substrate. It is demonstrated for the first time, from analytical‐scale experiments, that this microorganism hydroxylates a variety of simple n ‐alkanes (hexane through nonane) and cycloalkanes (cyclohexane and cyclooctane) to afford optically active alcohols in up to 99% enantiomeric excess ( ee ). In the case of the n ‐alkanes, the ω‐1, ω‐2 and ω‐3 regioisomers were obtained. This enzymatic activity is unprecedented for Bacillus megaterium strains and is generally rarely observed in bacteria.