Structure of the O-polysaccharide of Proteus mirabilis O38 containing 2-acetamidoethyl phosphate and N-linked D-aspartic acid.
The O-antigen of Proteus mirabilis O38 was found to be unique among bacterial polysaccharides and to have the following structure: [carbohydrate structure in text] where D-Qui4N(Ac-D-Asp) is 4-(N-acetyl-D-aspart-4-ylamino)-4,6-dideoxy-D-glucose and AcEtnP is 2-acetamidoethyl phosphate. Neither of these entities have been hitherto found in natural polysaccharides. Structural studies were performed using 1D and 2D NMR spectroscopy, including experiments run in an H2O/D2O mixture to reveal correlations for NH protons. In addition, dephosphorylation, carboxyl reduction and selective cleavages were applied. Solvolysis of the polysaccharide with anhydrous HF gave an alpha-D-GlcNAc-(1-->3)-D-Qui4N(Ac-D-Asp) disaccharide. Solvolysis with trifluoromethanesulfonic (triflic) acid afforded D-GlcNAc6(AcEtnP), thus showing the suitability of this reagent for the preparation of phosphorylated sugar derivatives.
Kondakova
Anna N
AN
ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, Moscow 119991, Russia.
Senchenkova
Sof'ya N
SN
Gremyakov
Andrei I
AI
Shashkov
Alexander S
AS
Knirel
Yuriy A
YA
Fudala
Rafal
R
Kaca
Wieslaw
W
D000586:Amination; D001224:Aspartic Acid / Q000737:chemistry*; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010766:Phosphorylation; D011134:Polysaccharides / Q000737:chemistry* / Q000302:isolation & purification; D011513:Proteus mirabilis / Q000737:chemistry*; D013403:Sugar Phosphates / Q000032:analysis* / Q000737:chemistry
D011134:Polysaccharides; D013403:Sugar Phosphates; D001224:Aspartic Acid