Synthesis of 4-nitrophenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- (1-->2)-O-(6-O-methyl-alpha-D-mannopyranosyl)-(1-->6)-beta-D- glucopyranoside and its 4',6'-di-O-methyl analog. Potential inhibitors of N-acetylglucosaminyl-transferase V (GnT-V).
O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1-->2) -3,4 - di-O-acetyl-6-O-methyl-alpha-D-mannopyranosyl bromide and O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)- (1-->2)-3-O-acetyl-4,6-di-O-methyl-alpha-D-mannopyranosyl bromide were each condensed with 4-nitrophenyl 2,3-di-O-acetyl-beta-D-glucopyranoside, and the products were deprotected to yield, respectively, beta-D-Glc p NAc-(1-->2)-6-O-Me-alpha-D-Man p-(1-->6)-beta-D-Glc p and beta-D-Glc p NAc-(1-->2)-4,6-di-O-Me-alpha-D-Man p-(1-->6)-beta-D-Glc p, as their 4-nitrophenyl glycosides. These trisaccharides are expected to function as inhibitors for N-acetylglucosaminyltransferase V.
Khan
S H
SH
Department of Gynecologic Oncology, Roswell Park Cancer Institute, Buffalo, New York 14263.
Matta
K L
KL
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D017351:N-Acetylglucosaminyltransferases / Q000037:antagonists & inhibitors*; D009904:Optical Rotation; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology
D007202:Indicators and Reagents; D014312:Trisaccharides; C081966:4-nitrophenyl O-(2-acetamido-2-deoxyglucopyranosyl)-(1-2)-O-(6-O-methylmannopyranosyl)-(1-6)-glucopyranoside; C081967:4-nitrophenyl O- (2-acetamido-2-deoxyglucopyranosyl)-(1-2)-O-(4,6-di-O-methylmannopyranosyl)-(1-6)-glucopyranoside; D017351:N-Acetylglucosaminyltransferases; C052254:alpha-1,6-mannosylglycoprotein beta 1,6-N-acetylglucosaminyltransferase