(S)-2-amino-1,3-propanediol-3-phosphate-carrying diradylglyceroglycolipids. Novel major membrane lipids of Clostridium innocuum.

摘要: Two novel aminophosphoglycolipids (I, II) were isolated from Clostridium innocuum which constitute 51% (I) and 15% (II) of total polar membrane lipids. The structures, established by quantitative methylation analyses, fast-atom-bombardment mass spectrometry, one- two-dimensional NMR spectroscopy, are S-2-amino-1,3-propanediol-3-phospho-6-alpha-D-galactopyranosyl(1-2)alpha -D- glucopyranosyl(1-3)diradylglycerol an acylated derivative that carries additional fatty acid ester on O6 the glucosyl moiety. stereochemical configuration 2-amino-1,3-propanediol 3-phosphate residue was elucidated conversion to N-acetylserine 3-phosphate, with subsequent release identification L-serine HPLC. In addition diacylglycerol species, both contain 15-32% 1-O-(alk-1-enyl)-2-O-acyl-glycerol species in C14, C16, C18 vinyl ether combined predominantly unsaturated C16 ester. Hydrogenation required desorb alkyl, acyl-substituted spectrometry. made it further possible alkyl glycerols hydrolysis locate bond at O1 glycerol contrast glycerophosphoglycolipids other Gram-positive bacteria, metabolically not related lipoteichoic C. serve, therefore, exclusively as major components. Their large abundance among lipids suggests bilayer-forming physicochemical properties.