Synthesis of the tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium.
An alpha-glycoside of the tetrasaccharide sequence beta-Ant-(1-->3)-alpha-l-Rhap-(1-->3)-alpha-l-Rhap-(1-->2)-alpha-l-Rhap whose aglycon allows conjugation to suitable carriers was synthesized. The NMR characteristics of the compound are virtually identical with those of the alpha-anomer of the tetrasaccharide isolated from the major glycoprotein of the Bacillus anthracis exosporium. Thus, the correct structure of the natural product has been proven by chemical synthesis.
Saksena
Rina
R
National Institute of Diabetes and Digestive and Kidney Disease/LMC, National Institutes of Health, Bethesda, MD 20892-0815, USA.
Adamo
Roberto
R
Kovác
Pavol
P
D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D001408:Bacillus anthracis / Q000737:chemistry*; D001426:Bacterial Proteins / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000302:isolation & purification
D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D006023:Glycoproteins; D009844:Oligosaccharides