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Total Synthesis of the Complete Protective Antigen of Vibrio cholerae O139.

ABSTRACT: The first chemical synthesis of the complete protective O-antigen of a human-disease-causing pathogenic bacterium is described. The synthesis involved a protecting-group strategy that facilitated the regioselectivity of the key transformations, stereoselective glycosylation reactions, and enabled the one-step global deprotection of the completely assembled, fully protected, phosphorylated hexasaccharide by hydrogenation/hydrogenolysis. The final amino-group-functionalized, linker-equipped antigen was obtained in a form ready for conjugation to suitable carriers, for example, proteins, to yield immunogens.

SUBMITTER: Soliman SE

PROVIDER: S-EPMC5165651 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Total Synthesis of the Complete Protective Antigen of Vibrio cholerae O139.

Soliman Sameh E SE Kováč Pavol P

Angewandte Chemie (International ed. in English) 20160914 41

The first chemical synthesis of the complete protective O-antigen of a human-disease-causing pathogenic bacterium is described. The synthesis involved a protecting-group strategy that facilitated the regioselectivity of the key transformations, stereoselective glycosylation reactions, and enabled the one-step global deprotection of the completely assembled, fully protected, phosphorylated hexasaccharide by hydrogenation/hydrogenolysis. The final amino-group-functionalized, linker-equipped antige ...[more]

PMID: 27623688

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