Concise synthesis of the pentasaccharide O-antigen corresponding to the Shiga toxin producing Escherichia coli O171.
An expedient total synthesis of a pentasaccharide as its 4-methoxyphenyl glycoside corresponding to the Shiga toxin producing Escherichia coli O171 has been achieved for the first time in excellent yield. Most of the glycosylation steps are highly stereoselective. Stereoselective glycosylation of sialic acid derivative was obtained exploiting the nitrile effect of the solvent used.
Mandal
Pintu Kumar
PK
Division of Molecular Medicine, Bose Institute, A.J.C. Bose Birth Centenary Campus, P-1/12, C.I.T. Scheme VII-M, Kolkata 700 054, India.
Misra
Anup Kumar
AK
D006031:Glycosylation; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D054323:Shiga-Toxigenic Escherichia coli / Q000737:chemistry*; D013237:Stereoisomerism
D009570:Nitriles; D019081:O Antigens; D009844:Oligosaccharides; D019158:N-Acetylneuraminic Acid