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

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 commo...

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Bibliographic Details
Published in:Chembiochem : a European journal of chemical biology 2015-08, Vol.16 (12), p.1764-1770
Main Authors: Bodlenner, Anne, Liu, Wenjun, Hirsch, Guillaume, Schaeffer, Philippe, Blumenberg, Martin, Lendt, Ralf, Tritsch, Denis, Michaelis, Walter, Rohmer, Michel
Format: Article
Language:English
Subjects:
bacteriohopanetetrol
biosynthesis
Cell-Free System
Chemical Sciences
Crystal structure
isotopic labeling
Methylobacterium - chemistry
Molecular Structure
Organic chemistry
ribosylhopane
terpenoids
Triterpenes - chemistry
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Summary: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. 2H‐labelled ribosylhopane was converted into 2H‐labelled bacteriohopanetetrol by a cell‐free system derived from Methylobacterium organophilum in the presence of NADPH. This afforded the first direct evidence of its intermediacy in the C35 hopanoid biosynthetic pathway.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.201500021