title: Neoglycoconjugates from synthetic tetra- and hexasaccharides that mimic the terminus of the O-PS of Vibrio cholerae O:1, serotype Inaba.
abstract: A glycosyl acceptor and a glycosyl donor having the N-3-deoxy-L-glycero-tetronic acid side chain already attached have been prepared and used for the synthesis of the di-through to the hexasaccharide that mimic the upsteam terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Inaba. The target tetra- and the hexasaccharide, which were obtained in the form of 5-methoxycarbonylpentyl glycosides, were linked to BSA using squaric acid diester chemistry. The conjugation reactions were monitored by surface enhanced laser desorption ionization-time of flight mass spectrometry (SELDI-TOF MS). This allowed the progression of the conjugation of the synthetic oligosaccharides in a controlled way and termination of the reaction when the desired molar hapten/BSA ratio had been reached, yielding neoglycoconjugates with predetermined carbohydrate/carrier ratios. The ability to monitor the conjugation by the SELDI-TOF MS technique made it possible to prepare, from one hapten in a one-pot reaction, several neoglycoconjugates having different, predetermined carbohydrate/carrier ratios.
authors.affiliation: NIDDK, LMC, National Institutes of Health, Bethesda, MD 20892, USA.
authors.forename: Xingquan
authors.initials: X
authors.lastname: Ma
authors.forename: Rina
authors.initials: R
authors.lastname: Saksena
authors.forename: Anatoly
authors.initials: A
authors.lastname: Chernyak
authors.forename: Pavol
authors.initials: P
authors.lastname: Kovác
mesh_terms: D002240:Carbohydrate Sequence; D006001:Glycoconjugates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*; D014734:Vibrio cholerae / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D009844:Oligosaccharides