Open AccessStructure elucidation and biosynthesis of 31‐methylhopanoids from Acetobacter europaeus
Author(s) -
Simonin Pascale,
Tindall Brian,
Rohmer Michel
Publication year - 1994
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1994.00765.x
Subject(s) - hopanoids , methylation , moiety , methyl group , biosynthesis , chemistry , acetobacter , stereochemistry , methionine , ether , biochemistry , biology , organic chemistry , group (periodic table) , amino acid , gene , paleontology , fermentation , source rock , structural basin
Apart from a mixture of bacteriohopanetetrols already found in other Acetobacter species, four new 3β‐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 ‐ 2 H 3 ]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.