Structure of the O-polysaccharide of Idiomarina zobellii KMM 231T containing two unusual amino sugars with the free amino group, 4-amino-4,6-dideoxy-D-glucose and 2-amino-2-deoxy-L-guluronic acid |
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Authors: | Kilcoyne Michelle Perepelov Andrei V Tomshich Svetlana V Komandrova Nadezhda A Shashkov Alexander S Romanenko Ludmila A Knirel Yuriy A Savage Angela V |
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Institution: | Department of Chemistry, National University of Ireland, Galway, Ireland. |
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Abstract: | Mild acid degradation of the lipopolysaccharide of the bacterium Idiomarina zobellii, type strain KMM 231T, with aq 2% HOAc at 100 degrees C, yielded an oligosaccharide, which represents one repeating unit of the O-polysaccharide. A polysaccharide was obtained by mild base degradation of the lipopolysaccharide. The following structure of the O-polysaccharide was elucidated by 1H and 13C NMR spectroscopy of the oligosaccharide and base-degraded lipopolysaccharide, including COSY, TOCSY, ROESY, 1H, 13C HSQC, HSQC-TOCSY and HMBC experiments: -->3)-alpha-D-Quip4N-(1-->4)-alpha-D-GlcpA-(1-->6)-alpha-D-GlcpNAc-(1-->4)-alpha-L-GulpNA-(1-->3)-beta-D-FucpNAc-(1-->] The O-polysaccharide is distinguished by the presence of two unusual amino sugars, 4-amino-4,6-dideoxy-D-glucose (D-Qui4N) and 2-amino-2-deoxy-L-guluronic acid (L-GulNA), both having the free amino group. The unexpectedly high acid lability of the glycosidic linkage of 2-acetamido-2,6-dideoxy-D-galactose (D-FucNAc) could be associated with the presence of a free amino group adjacent to the site of attachment of FucNAc to Qui4N. |
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Keywords: | Idiomarina zobellii Marine bacteria Lipopolysaccharide Bacterial polysaccharide structure l-guluronic acid" target="_blank">2-Amino-2-deoxy-l-guluronic acid 4-Amino-4 d-glucose" target="_blank">6-dideoxy-d-glucose |
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