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Stereochemical Investigations Reveal the Mechanism of the Bacterial Activation of n ‐Alkanes without Oxygen
Author(s) -
Jarling René,
Sadeghi Masih,
Drozdowska Marta,
Lahme Sven,
Buckel Wolfgang,
Rabus Ralf,
Widdel Friedrich,
Golding Bernard T.,
Wilkes Heinz
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106055
Subject(s) - hexane , hydrocarbon , chemistry , alkane , oxygen , oxygen atom , hydrogen , bacteria , strain (injury) , stereochemistry , photochemistry , organic chemistry , molecule , biology , anatomy , genetics
Anaerobic growth of the bacterium strain HxN1 with n ‐hexane gives nearly equal amounts of (2 R ,1′ R )‐ and (2 S ,1′ R )‐(1‐methylpentyl)succinate, which are formed by the radical addition of the hydrocarbon to fumarate (see scheme). The highly selective attack on the pro‐ S hydrogen atom at C2 of n ‐hexane is associated with inversion of the configuration at C2 during binding to fumarate and exhibits isotopic discrimination against a C 2 H bond.
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