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C 35 Hopanoid Side Chain Biosynthesis: Reduction of Ribosylhopane into Bacteriohopanetetrol by a Cell‐Free System Derived from Methylobacterium organophilum
Author(s) -
Bodlenner Anne,
Liu Wenjun,
Hirsch Guillaume,
Schaeffer Philippe,
Blumenberg Martin,
Lendt Ralf,
Tritsch Denis,
Michaelis Walter,
Rohmer Michel
Publication year - 2015
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201500021
Subject(s) - hopanoids , side chain , stereochemistry , biosynthesis , chemistry , moiety , biochemistry , triterpene , biology , organic chemistry , enzyme , medicine , paleontology , alternative medicine , pathology , structural basin , source rock , polymer
The major bacterial triterpenoids of the hopane series each consist of a C 30 triterpene hopane moiety and an additional nonterpene C 5 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.