Nature, type of linkage, and absolute configuration of (hydroxy) fatty acids in lipopolysaccharides from Xanthomonas sinensis and related strains

Abstract

The fatty acids present in lipopolysaccharides from Xanthomonas sinensis were identified as decanoic, 9-methyl-decanoic, 2-hydroxy-9-methyl-decanoic, 2-hydroxy-9-methyl-decanoic, D-3-hydroxy-decanoic, D-3-hydroxy-9-methyl-decanoic, D-3-hydroxy-dodecanoic, and D-3-hydroxy-11-methyl-dodecanoic acid. These fatty acids occur in the lipid A component where they are bound through ester and amide linkages to glucosamine residues. All types of fatty acids are ester bound; however, part of D-3-hydroxy-dodecanoic and D-3-hydroxy-11-methyl-dodecanoic acid is also involved in amide linkage. The hydroxyl groups of ester-linked 3-hydroxy fatty acids are not substituted. Similar fatty acid patterns were obtained from lipopolysaccharides of nine other Xanthomonas species.