methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-6-O-(methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-α-D-neuraminate-2-yl)-β-D-glucopyranoside | 329323-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-6-O-(methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-α-D-neuraminate-2-yl)-β-D-glucopyranoside
• CAS: 329323-64-0
• 化学式: C₄₁H₄₈N₄O₁₉
• 分子量: 900.848
• InChiKey: UXIGLTXQKAOIQI-GGJZLVJWSA-N

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-6-O-(methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-α-D-neuraminate-2-yl)-β-D-glucopyranoside 在 1,3-丙二硫醇 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 methyl 2-amino-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：

  、 sialyl xanthate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 以51 mg的产率得到methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-6-O-(methyl 4,7,8,9-tetra-O-acetyl-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