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.
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.
Kilcoyne
Michelle
M
Department of Chemistry, National University of Ireland, Galway, Ireland.
Perepelov
Andrei V
AV
Tomshich
Svetlana V
SV
Komandrova
Nadezhda A
NA
Shashkov
Alexander S
AS
Romanenko
Ludmila A
LA
Knirel
Yuriy A
YA
Savage
Angela V
AV
D000606:Amino Sugars / Q000032:analysis* / Q000737:chemistry*; D020563:Gammaproteobacteria / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000032:analysis* / Q000737:chemistry; D006603:Hexuronic Acids / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019081:O Antigens / Q000737:chemistry*
C492813:2-amino-2-deoxyguluronic cid; C492812:4-amino-4,6-dideoxyglucose; D000606:Amino Sugars; D006603:Hexuronic Acids; D019081:O Antigens; D005944:Glucosamine