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Total Synthesis of the Complete Protective Antigen of Vibrio cholerae O139
Author(s) -
Soliman Sameh E.,
Kováč Pavol
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606116
Subject(s) - vibrio cholerae , hydrogenolysis , glycosylation , chemistry , regioselectivity , linker , stereoselectivity , antigen , protecting group , combinatorial chemistry , bacteria , biochemistry , catalysis , biology , organic chemistry , immunology , alkyl , computer science , operating system , genetics
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.