Total Synthesis of the Complete Protective Antigen of Vibrio cholerae O139.
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.
NIDDK, LBC, Section on Carbohydrates, National Institutes of Health (NIH), Bethesda, MD, 20892-0815, USA.|Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, 21321, Egypt.
Sameh E
SE
Soliman
NIDDK, LBC, Section on Carbohydrates, National Institutes of Health (NIH), Bethesda, MD, 20892-0815, USA. kpn@helix.nih.gov.
Pavol
P
Kováč
D002236:Carbohydrate Conformation; D019081:O Antigens / Q000737:chemistry*; D041242:Vibrio cholerae O139 / Q000737:chemistry*
D019081:O Antigens
O-specific antigens; glycosylation; oligosaccharides; pathogenic bacteria; stereoselectivity