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Phosphatidylkojibiosyl diglyceride: Metabolism and function as an anchor in bacterial cell membranes
Author(s) -
Pieringer Ronald A.,
Ganfield MongChing W.
Publication year - 1975
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532448
Subject(s) - diglyceride , lipoteichoic acid , glycerol , chemistry , biochemistry , monoglyceride , teichoic acid , fatty acid , enzyme , bacteria , biology , peptidoglycan , genetics , staphylococcus aureus
The recently discovered phosphoglycolipid, phosphatidylkojibiosyl diglyceride (PKD), was first observed as a biosynthetic by‐product of glucosyl diglyceride metabolism in Streptococcus faecalis (faecium) ATCC 9790. Its structure is 1,2‐diacyl‐3‐O(2′‐O‐α‐D‐glucopyranosyl‐6′‐O‐phosphoryl‐[1″,2″‐diacyl‐3″‐O‐ sn ‐glycerol]‐α‐D‐glucopyranosyl)‐ sn ‐glycerol. The biosynthesis of phosphatidylkojibiosyl diglyceride occurs by a novel transphosphatidylation reaction in which a phosphatidyl group is transferred from diphosphatidyl glycerol to the primary alcohol function at the 6 position of the internal glucose of kojibiosyl diglyceride. The reaction is catalyzed by a membrane‐derived enzyme. Phosphatidylkojibiosyl diglyceride is bound covalently through a phosphodiester bond to the polyglycerol phosphate moiety of membrane lipoteichoic acid from S. faecalis . Phosphatidylkojibosyl diglyceride has four nonpolar long chain fatty acyl groups and appears to have the necessary physico‐chemical properties to anchor the long hydrophilic glycerol phosphate polymer of lipoteichoic acid to the hydrophobic environment of the membrane of S. faecalis and probably other gram‐positive bacteria as well.