Studies on vaccines against cholera. Synthesis of neoglycoconjugates from the hexasaccharide determinant of Vibrio cholerae O:1, serotype Ogawa, by single-point attachment or by attachment of the hapten in the form of clusters.
The terminal hexasaccharide of the O-antigen of Vibrio cholerae O:1, serotype Ogawa, has been synthesized in the form of a glycoside whose aglycon (linker) allows conjugation to carrier proteins by reductive amination. The conjugate obtained from direct, single-point attachment of the linker-equipped hapten to chicken serum albumin (CSA) contained seven hapten residues/CSA. A neoglycoconjugate containing the carbohydrate antigen in the form of clusters was obtained using, as a hapten subcarrier, an oligopeptide containing 16 amino groups. It was treated with a limited amount of hapten, to give a hapten-carrying subcarrier (HCS). Subsequent conjugation of HCS to CSA, using squaric acid diethyl ester as a conjugation reagent, gave a cross-linked, glycocluster conjugate containing 51% (w/w) of the carbohydrate.
Zhang
J
J
National Institutes of Health, NIDDK, Laboratory of Medicinal Chemistry, Bethesda, MD 20892-0815, USA.
Kovác
P
P
D002240:Carbohydrate Sequence; D022121:Cholera Vaccines / Q000276:immunology; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000276:immunology; D006241:Haptens / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry / Q000276:immunology; D011135:Polysaccharides, Bacterial / Q000276:immunology; D012703:Serotyping; D014734:Vibrio cholerae / Q000737:chemistry / Q000276:immunology*
D022121:Cholera Vaccines; D006001:Glycoconjugates; D006241:Haptens; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial