Substrate range of benzylsuccinate synthase from Azoarcus sp. strain T.

TitleSubstrate range of benzylsuccinate synthase from Azoarcus sp. strain T.
Publication TypeJournal Article
Year of Publication1999
AuthorsBeller, HR, Spormann AM
JournalFEMS microbiology letters
Volume178
Issue1
Pagination147-53
Date Published1999 Sep 1
ISSN0378-1097
KeywordsCarbon-Carbon Lyases, Fumarates, Gram-Negative Facultatively Anaerobic Rods, Toluene
AbstractBenzylsuccinate synthase, which catalyzes the anaerobic addition of the methyl carbon of toluene to fumarate, has recently been reported in several denitrifying and sulfate-reducing, toluene-degrading bacteria. In substrate range studies with partially purified benzylsuccinate synthase from denitrifying Azoarcus sp. strain T, benzylsuccinate analogs were observed as a result of fumarate addition to the following toluene surrogates: xylenes, monofluorotoluenes, benzaldehyde, and 1-methyl-1-cyclohexene (but not 4-methyl-l-cyclohexene or methylcyclohexane). Benzylsuccinate was also observed as a result of toluene addition to maleate, but no products were observed from assays with toluene and either crotonate or trans-glutaconate. Toluene-maleate addition, like toluene-fumarate addition, resulted in highly stereospecific formation of the (+)-benzylsuccinic acid enantiomer [(R)-2-benzyl-3-carboxypropionic acid]. The previously reported finding that the methyl H atom abstracted from toluene is retained in the succinyl moiety of benzylsuccinate was found to apply to several toluene surrogates. The implications of these observations for the mechanism of benzylsuccinate synthase will be discussed.
Alternate JournalFEMS Microbiol. Lett.
0 November 24, 2010