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( S )‐2‐Amino‐1,3‐propanediol‐3‐phosphate‐carrying diradylglyceroglycolipids
Author(s) -
FISCHER Werner,
HARTMANN Rudolf,
PETERKATALINIĆ Jasna,
EGGE Heinz
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.tb19065.x
Subject(s) - chemistry , moiety , fast atom bombardment , alkyl , fatty acid , hydrolysis , ether , double bond , stereochemistry , mass spectrometry , organic chemistry , chromatography
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 and methylation analyses, fast‐atom‐bombardment mass spectrometry, and one‐ and two‐dimensional NMR spectroscopy, are (I) S ‐2‐amino‐1,3‐propanediol‐3‐phospho‐6‐α‐ d ‐galactopyranosyl(1‐2)α‐ d ‐glucopyranosyl(1‐3)diradylglycerol and (II) an acylated derivative of (I) that carries an additional fatty acid ester on O6 of the glucosyl moiety. The stereochemical configuration of the 2‐amino‐1,3‐propanediol 3‐phosphate residue was elucidated by conversion to N ‐acetylserine 3‐phosphate, with subsequent release and identification of l ‐serine by HPLC. In addition to diacylglycerol species, both aminophosphoglycolipids contain 15–32% 1‐ O ‐(alk‐1‐enyl)‐2‐ O ‐acyl‐glycerol species in which C 14 , C 16 , and C 18 vinyl ether are combined predominantly with unsaturated C 16 and C 18 fatty acid ester. Hydrogenation of the vinyl ether was required to desorb the alkyl, acylsubstituted species in fast‐atom‐bombardment mass spectrometry. Hydrogenation made it further possible to release the alkyl glycerols by acid hydrolysis and to locate the ether bond at O1 of the glycerol moiety. In contrast to the glycerophosphoglycolipids of other Gram‐positive bacteria, the aminophosphoglycolipids are metabolically not related to the lipoteichoic acid of C. innocuum and serve, therefore, exclusively as major membrane components. Their large abundance among membrane lipids suggests bilayer‐forming physicochemical properties.

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