p-nitrophenyl 2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranoside | 84564-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranoside
• CAS: 84564-20-5
• 化学式: C₂₈H₂₆N₂O₁₀
• 分子量: 550.522
• InChiKey: YVGXADBBTGQGDW-JWJHGQTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  163.53
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 4-nitrophenyl 2-acetamido-2-deoxy-6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-glucopyranoside
  参考文献：
  名称：

  Design and synthesis of a multivalent homing device for targeting to murine CD22

  摘要：

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00224-8
• 作为产物：
  描述：

  4-硝基苯基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷 在 溶剂黄146 作用下， 以 吡啶 、 水 为溶剂， 反应 2.25h， 生成 p-nitrophenyl 2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  合成三种二糖以制备带有已知在糖蛋白上发生的免疫决定簇的免疫原

  摘要：

  将对硝基苯基2-乙酰氨基-3,6-二-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷与2,3,4,6-四-O-苄基-α-D-吡喃半乳糖基溴缩合，产物脱保护，二糖苷转变为对三氟乙酰氨基苯基2-乙酰氨基-2-脱氧-4-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖苷。将对硝基苯基3-O-苯甲酰基-4,6-二-O-亚苄基-α-D-甘露吡喃糖苷与3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D缩合-吡喃葡萄糖基溴化物，然后将产物脱保护，得到对硝基苯基2-O-（2-乙酰氨基-2-脱氧β-D-吡喃葡萄糖基）-α-D-甘露吡喃糖苷。将对硝基苯基2-乙酰氨基-3,4-二-O-苯甲酰基-2-脱氧-β-D-吡喃葡萄糖苷与2,3,4-三-O-苄基-α-L-呋喃核糖基溴缩合，还原，三氟乙酰化和脱保护后，

  DOI：

  10.1016/0008-6215(82)85025-8