Preparation of synthetic glycoconjugates as potential vaccines against Shigella flexneri serotype 2a disease
- 26 April 2004
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 2 (10) , 1518-1527
- https://doi.org/10.1039/b400986j
Abstract
The synthesis of three neoglycopeptides incorporating carbohydrate haptens, differing in length, covalently linked to a non natural universal T helper peptide is disclosed. They were synthesized according to a blockwise strategy based on the condensation of appropriate di-, tri-, and tetrasaccharide trichloroacetimidate donors onto an azidoethyl 2-acetamido-2-deoxy-β-D-glucopyranoside acceptor. Use of thiol–maleimide coupling chemistry allowed site-selective efficient conjugation.Keywords
This publication has 70 references indexed in Scilit:
- Induction of carbohydrate‐specific antibodies in HLA‐DR transgenic mice by a synthetic glycopeptide: a potential anti cancer vaccine for human useChemical Biology & Drug Design, 2003
- Large-Scale Synthesis of a Lewis b Tetrasaccharide Derivative, its Acrylamide Copolymer, and Related DI- and Trisaccharides for Use in Adhesion Inhibition Studies with Helicobacter Pylori.Journal of Carbohydrate Chemistry, 1996
- Synthesis of the Trisaccharide α-l-Rha-(1-2)-α-l-Rha-(1-2)-α-L-Rha with a Dioxolane-Type Spacer-Arm1Journal of Carbohydrate Chemistry, 1996
- Development of high potency universal DR-restricted helper epitopes by modification of high affinity DR-blocking peptidesImmunity, 1994
- Simultaneous multiple synthesis and selective conjugation of cyclized peptides derived from a surface loop of a meningococcal class 1 outer membrane proteinInternational Journal of Peptide and Protein Research, 1994
- Preparation of a well-defined sugar-peptide conjugate: a possible approach to a synthetic vaccine against neisseria meningitidisBioorganic & Medicinal Chemistry Letters, 1991
- Mammosides B and H1, new ionophoric resin-glycosides from the tuber of Merremia mammosa, an indonesian folk medicine.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- The Synthesis of 4-O-α-D-Glucopyranosyl-L-rhamnopyranoseCanadian Journal of Chemistry, 1974
- The allyl ether as a protecting group in carbohydrate chemistry. Part IIJournal of the Chemical Society C: Organic, 1968
- 322. The reactions of substituted maleimides with thiolsJournal of the Chemical Society, 1949