Structure elucidation and biosynthesis of 31-methylhopanoids from Acetobacter europaeus. Studies on a new series of bacterial triterpenoids.
Apart from a mixture of bacteriohopanetetrols already found in other Acetobacter species, four new 3 beta-methylhopanoids have been isolated from Acetobacter europaeus. All of them present an ether linkage between a bacteriohopanetetrol or a bacteriohopanepentol and a carbapseudopentose moiety often found in bacterial hopanoids. Three of these ethers were shown by comparison with synthetic reference hopanoids to posess a supplementary methyl group at C31. This novel series of methylhopanoids may be the precursor of yet unidentified molecular fossils found in sediments. [methyl-2H3]Methionine was efficiently incorporated into the 31-methylhopanoids with retention of all three deuterium atoms in the transferred methyl group. This labelling pattern might be consistent with a rather rarely found methylation reaction of an enol.
Simonin
P
P
Laboratoire de Chimie Microbienne, CNRS-URA 135, Ecole Nationale Supérieure de Chimie de Mulhouse, Mulhouse, France.
Tindall
B
B
Rohmer
M
M
D000091:Acetobacter / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
D014315:Triterpenes