Synthesis of 2'-azidoethyl trisaccharide, alpha-D-Gal-(1-->2)-6d-alpha-D-altro-Hepp-(1-->3)-beta-D-GlcNAc, an O-antigenic repeating unit of C. jejuni O:23 and O:36.
A trisaccharide, the O-antigenic repeating unit of C. jejuni serotype O:23 and O:36, was synthesized as a 2'-azidoethyl glycoside by block addition of perbenzylated thiogalactoside donors to alpha-altroHepp-(1-->3)-GlcNPhth disaccharide acceptor in presence of IDCP promoter. The alpha-linked altroheptopyranoside moiety in the glycosyl acceptor was effectively prepared by Swern oxidation of alpha-mannohepp-(1-->3)-GlcNPhth disaccharide followed by mild reduction with NaCNBH3.
Yun
Mikyung
M
Department of Chemistry, Soongsil University, Seoul 156-743, Korea.
Yoon
Shinsook
S
Shin
Youngsook
Y
Chun
Keun Ho
KH
Nam Shin
Jeong E
JE
D001386:Azides / Q000138:chemical synthesis*; D016123:Campylobacter jejuni / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D012015:Reference Standards; D012997:Solvents; D014312:Trisaccharides / Q000138:chemical synthesis*
D001386:Azides; D007202:Indicators and Reagents; D019081:O Antigens; D012997:Solvents; D014312:Trisaccharides