title: Hemisynthesis of deuteriated adenosylhopane and conversion into bacteriohopanetetrol by a cell-free system from Methylobacterium organophilum.
abstract: Adenosylhopane is a putative precursor of the widespread bacterial C35 biohopanoids. A concise and flexible hemisynthesis of adenosylhopane has been developed including as key steps a cross metathesis between two olefins containing either the hopane moiety or a protected adenosine derivative and a subsequent diimide reduction of the resulting olefin. Reduction by deuteriated diimide allowed deuterium labelling. This synthetic protocol represents a versatile tool to access to deuteriated composite bacterial hopanoids required for biosynthetic studies. Deuteriated adenosylhopane was thus converted into bacteriohopanetetrol by a crude cell-free system from Methylobacterium organophilum in the presence of NADPH, showing for the first time the precursor to product relationship between these two bacterial metabolites.
authors: Université de Strasbourg/CNRS, Institut Le Bel, 4 rue Blaise Pascal, F 67070 Strasbourg, Cedex, France. mirohmer@unistra.fr.
authors: Wenjun
authors: W
authors: Liu
authors: Anne
authors: A
authors: Bodlenner
authors: Michel
authors: M
authors: Rohmer
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D020580:Methylobacterium / Q000737:chemistry*; D008968:Molecular Conformation; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014315:Triterpenes; C000601331:adenosylhopane; C054760:32,33,34,35-bacteriohopanetetrol; D000241:Adenosine