Analysis of the novel benzylsuccinate synthase reaction for anaerobic toluene activation based on structural studies of the product.

Abstract:

:Recent studies of anaerobic toluene catabolism have demonstrated a novel reaction for anaerobic hydrocarbon activation: the addition of the methyl carbon of toluene to fumarate to form benzylsuccinate. In vitro studies of the anaerobic benzylsuccinate synthase reaction indicate that the H atom abstracted from the toluene methyl group during addition to fumarate is retained in the succinyl moiety of benzylsuccinate. Based on structural studies of benzylsuccinate formed during anaerobic, in vitro assays with denitrifying, toluene-mineralizing strain T, we now report the following characteristics of the benzylsuccinate synthase reaction: (i) it is highly stereospecific, resulting in >95% formation of the (+)-benzylsuccinic acid enantiomer [(R)-2-benzyl-3-carboxypropionic acid], and (ii) active benzylsuccinate synthase does not contain an abstracted methyl H atom from toluene at the beginning or at the end of a catalytic cycle.

journal_name

J Bacteriol

journal_title

Journal of bacteriology

authors

Beller HR,Spormann AM

doi

10.1128/JB.180.20.5454-5457.1998

subject

Has Abstract

pub_date

1998-10-01 00:00:00

pages

5454-7

issue

20

eissn

0021-9193

issn

1098-5530

journal_volume

180

pub_type

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