Khan S H, Abbas S A, Matta K L
Department of Gynecologic Oncology, Roswell Park Memorial Institute, Buffalo, NY 14263.
Carbohydr Res. 1989 Oct 31;193:125-39. doi: 10.1016/0008-6215(89)85112-2.
Four different oligosaccharides containing the 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1----2)-alpha-D-mannopyran osy l sequence as a terminal disaccharide unit were synthesized, namely: 4-nitrophenyl O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----2)-O-alpha-D-mannopyranosyl-(1----6)-beta-D- mannopyranoside (27), 4-nitrophenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----2)-O-alpha-D-mann opy ranosyl - (1----6)-beta-D-glucopyranoside (29), allyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1----2)-alpha-D- mannopyranosyl-(1----6)-beta-D-glucopyranoside (31), and allyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----2)-O-alpha-D- mannopyranosyl-(1----6)-O-beta-D-glucopyranosyl-(1----4)-beta-D-gluco pyr anoside (33). A common glycosyl donor, namely, 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D- glucopyranosyl)-3,4,6-tri-O-acetyl-alpha-D-mannopyranosyl bromide was employed for the synthesis of 27, 29, 31, and 33, the structures of which were all established by 13C-n.m.r. spectroscopy.
合成了四种不同的低聚糖,它们含有2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-(1→2)-α-D-吡喃甘露糖基序列作为末端二糖单元,即:4-硝基苯基O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→2)-O-α-D-吡喃甘露糖基-(1→6)-β-D-吡喃甘露糖苷(27)、4-硝基苯基O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→2)-O-α-D-吡喃甘露糖基-(1→6)-β-D-吡喃葡萄糖苷(29)、烯丙基O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-(1→2)-α-D-吡喃甘露糖基-(1→6)-β-D-吡喃葡萄糖苷(31)和烯丙基O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→2)-O-α-D-吡喃甘露糖基-(1→6)-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖苷(33)。一种常见的糖基供体,即2-O-(2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-3,4,6-三-O-乙酰基-α-D-吡喃甘露糖基溴被用于合成27、29、31和33,它们的结构均通过13C-核磁共振光谱确定。