One-pot preparation of a series of glycoconjugates with predetermined antigen-carrier ratio from oligosaccharides that mimic the O-PS of Vibrio cholerae O:1, serotype Ogawa |
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Authors: | Saksena Rina Ma Xingquan Kovác Pavol |
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Affiliation: | Laboratory of Medicinal Chemistry, National Institute Diabets and Digestive and Kidney Diseases, National Institutes of Health, Building 8, Rm B1A24, Bethesda, MD 20892-0815, USA. |
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Abstract: | Di-through the pentasaccharide that mimic the upstream terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa were synthesized in the form of 5-methoxycarbonylpentyl glycosides and 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), which allowed conducting 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. This made it possible to prepare, from one hapten in a one-pot reaction, a series of neoglycoconjugates having different, predetermined carbohydrate-carrier ratios. The accuracy of molecular mass determination in SELDI-TOF MS analysis could be increased by using the carrier protein as the internal standard. |
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Keywords: | Vibrio cholerae O:1 Synthetic oligosaccharides Vaccine Neoglycoconjugate immunogens SELDI-TOF |
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