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Structural Analysis of the Deep Rough Lipopolysaccharide from Gram Negative Bacterium Alteromonas macleodii ATCC 27126 T : The First Finding of β‐Kdo in the Inner Core of Lipopolysaccharides
Author(s) -
Liparoti Valeria,
Molinaro Antonio,
Sturiale Luisa,
Garozzo Domenico,
Nazarenko Evgeny L.,
Gorshkova Raisa P.,
Ivanova Elena P.,
Shevcenko Luidmila S.,
Lanzetta Rosa,
Parrilli Michelangelo
Publication year - 2006
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/ejoc.200600489
Subject(s) - chemistry , alteromonas , lipid a , bacteria , lipopolysaccharide , hydrolysis , bacterial outer membrane , acylation , acid hydrolysis , stereochemistry , nuclear magnetic resonance spectroscopy , gram negative bacteria , biochemistry , escherichia coli , catalysis , medicine , genetics , gene , biology , endocrinology
Alteromonas macleodii ATCC 27126 T is a Gram‐negative marine bacterium isolated from a sea water sample collected from around the Hawaiian Islands. The structure of the lipooligosaccharide derived from its outer membrane has been fully determined using either alkaline or acid hydrolysis. Alkaline treatment, aimed at recovering the complete carbohydrate backbone, was carried out by mild hydrazinolysis (de‐ O ‐acylation) followed by de‐ N ‐acylation using hot KOH and furnished a single core glycoform. Mild acid hydrolysis was employed to obtain the lipid A moiety which was selectively de‐ O ‐acylated and analysed to determine its primary structure. The structural elucidation of both fractions was carried out by chemical analyses, 2D NMR spectroscopy and MALDI‐TOF mass spectrometry and revealed a novel lipooligosaccharide with an unusual structure. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)