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. 2015 Aug 17;16(12):1764-70.
doi: 10.1002/cbic.201500021. Epub 2015 Jul 14.

C35 Hopanoid Side Chain Biosynthesis: Reduction of Ribosylhopane into Bacteriohopanetetrol by a Cell-Free System Derived from Methylobacterium organophilum

Anne Bodlenner  1   2 , Wenjun Liu  1 , Guillaume Hirsch  1 , Philippe Schaeffer  3 , Martin Blumenberg  4   5 , Ralf Lendt  4 , Denis Tritsch  1 , Walter Michaelis  4 , Michel Rohmer  6
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C35 Hopanoid Side Chain Biosynthesis: Reduction of Ribosylhopane into Bacteriohopanetetrol by a Cell-Free System Derived from Methylobacterium organophilum

Anne Bodlenner et al. Chembiochem. .

Abstract

The major bacterial triterpenoids of the hopane series each consist of a C30 triterpene hopane moiety and an additional nonterpene C5 side chain derived from D-ribose and linked through its C-5 carbon atom to the hopane side chain. Bacteriohopanetetrol and aminobacteriohopanetriol are the most common representatives of this natural product series, adenosylhopane and ribosylhopane being putative precursors. Deuterium-labelled ribosylhopane was obtained by hemisynthesis and converted into deuterium-labelled bacteriohopanetetrol in the presence of NADPH, thus giving evidence of this as yet unknown precursor-to-product relationship in the bacterial hopanoid metabolic pathway.

Keywords: bacteriohopanetetrol; biosynthesis; isotopic labeling; ribosylhopane; terpenoids.

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