Synthesis of benzyl O-(2-O-methyl-beta-D-galactopyranosyl)-(1----3)-2- acetamido-2-deoxy-beta-D-glucopyranoside [benzyl 2'-O-methyllacto-N-bioside I], and its higher saccharide containing an O-(2-O-methyl-beta-D- galactopyranosyl)-(1----3)-2-acetamido-2-deoxy-beta-D-glucopyranosyl group as a potential substrate for (1---4)-alpha-L-fucosyltransferase.
Treatment of benzyl O-beta-D-galactopyranosyl-(1----3)-2-acetamido-2- deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside with tert-butylchlorodiphenylsilane afforded the 6'-O-tert-butyldiphenylsilyl ether, which was converted into the 3',4'-O-isopropylidene derivative. Methylation and subsequent removal of protecting groups afforded benzyl O-(2-O-methyl-beta-D-galactopyranosyl)- (1----3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (7). The trisaccharide methyl O-(2-O-methyl-beta-D-galactopyranosyl)-(1----3)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-beta-D-galactopyranosi de (17) and the tetrasaccharide O-(2-O-methyl-beta-D-galactopyranosyl)-(1----3)-O-(2-acetamido-2-deoxy-b eta-D- glucopyranosyl)-(1----3)-O-beta-D-galactopyranosyl-(1----4)-D-glucopyran ose (32), both containing the 2'-O-methyllacto-N-biose I unit at the nonreducing end, were synthesized, and the structures of 7, 17, and 32 were confirmed by 13C-n.m.r. spectroscopy.
Sarkar
A K
AK
Department of Gynecologic Oncology, Roswell Park Memorial Institute, Buffalo, New York 14263.
Jain
R K
RK
Matta
K L
KL
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D005647:Fucosyltransferases / Q000378:metabolism*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*
D004187:Disaccharides; D009844:Oligosaccharides; C065133:benzyl 2-acetamido-2-deoxy-3-O-(2-O-methyl-beta-galactosyl)-beta-glucopyranoside; D005647:Fucosyltransferases; C019818:3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase