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Determination of the Structure of the Lipid A Fraction from the Lipopolysaccharide of Pseudomonas Cichorii by Means of NMR and MALDI‐TOF Mass Spectrometry
Author(s) -
Molinaro Antonio,
Silipo Alba,
Lanzetta Rosa,
Parrilli Michelangelo,
Malvagna Paola,
Evidente Antonio,
Surico Giuseppe
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:18<3119::aid-ejoc3119>3.0.co;2-m
Subject(s) - chemistry , lipid a , disaccharide , fatty acid , mass spectrometry , phosphate , amide , glucosamine , carbon 13 nmr , nuclear magnetic resonance spectroscopy , stereochemistry , biochemistry , bacteria , organic chemistry , chromatography , genetics , biology
The chemical structure of lipid A from the lipopolysaccharide of the plant‐associated bacterium Pseudomonas cichorii , was elucidated by compositional analysis and spectroscopic methods (MALDI‐TOF and 2D NMR). The sugar’s backbone was constituted by the β‐(1′⇄6)‐linked D ‐glucosamine disaccharide 1‐phosphate. The lipid A fraction showed remarkable heterogeneity with respect to the fatty acid and phosphate composition. The major species are hexaacylated and pentaacylated lipid A, bearing the ( R )‐3‐hydroxydodecanoic acid [C12:0 (3OH)] in amide linkage and an ( R )‐3‐hydroxydecanoic [C10:0 (3OH)] in ester linkage while the secondary fatty acids are present as C12:0 and C12:0 (2‐OH). A nonstoichiometric phosphate substitution at position C‐4′ of the distal GlcN was detected. Interestingly, the pentaacyl lipid A is lacking a primary fatty acid, namely the C10:0 (3‐OH) at position C‐3′. A potential biological meaning of this peculiar lipid A is also suggested. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)