Open AccessChemical structure of the lipid A component of Plesiomonas shigelloides and its taxonomical significance
Author(s) -
Basu Sumanta,
Tharanathan Rudrapatnam N.,
Kontrohr Tivadar,
Mayer Hubert
Publication year - 1985
Publication title -
fems microbiology letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.899
H-Index - 151
eISSN - 1574-6968
pISSN - 0378-1097
DOI - 10.1111/j.1574-6968.1985.tb00753.x
Subject(s) - plesiomonas shigelloides , disaccharide , glucosamine , chemistry , lipid a , moiety , stereochemistry , amide , biochemistry , chemical structure , lipopolysaccharide , organic chemistry , bacteria , biology , genetics , endocrinology
The chemical structure of the lipid A moiety of the lipopolysaccharide of the type strain of Plesiomonas shigelloides was elucidated. It consists of a β‐(1 → 6)‐linked glucosamine disaccharide carrying phosphate groups at C‐1 of the reducing and at C‐4′ of the non‐reducing glucosamine. It contains a total of 6 residues of fatty acids, 2 amide‐linked and 4 ester‐linked. The amino groups of the backbone disaccharide are N ‐acylated by substituted 3‐hydroxyacyl residues: at the reducing glucosamine by 3‐O‐(14:0)14:0; and at the non‐reducing glucosamine by 3‐O‐(12:0)14:0. Two residues of 3‐hydroxytetradecanoic acid are linked to C‐3 and C‐3′ of the glucosamine residues; the hydroxy groups of these ester‐linked 3‐hydroxytetradecanoic acids are unsubstituted. In free lipid A, the hydroxyl groups at C‐4 and C‐6′ are unsubstituted, indicating that the 2‐keto‐3‐deoxyoctonic acid (KDO) is linked to C‐6′ of the non‐reducing glucosamine, as was shown with enterobacterial lipid A. The taxonomical significance of these structural details is discussed.