1-azido-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 212896-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-azido-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-(2-Azidoethoxy)ethyl-2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[2-(2-azidoethoxy)ethoxy]oxan-2-yl]methyl acetate
• CAS: 212896-43-0
• 化学式: C₁₈H₂₈N₄O₁₀
• 分子量: 460.441
• InChiKey: RYGROQIXTIVQGJ-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-azido-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(2-Azidoethoxy)ethyl-2-acetamido-2-deoxy-beta-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium azide 、 3 A molecular sieve 、 四乙基溴化铵 、 mercury(II) iodide 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-azido-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and modification of spacered glycosides of N-acetylglucosamine

  摘要：

  DOI：

  10.1007/bf02254805

文献信息

• Design and synthesis of a multivalent homing device for targeting to murine CD22
  作者：Leo A.J.M. Sliedregt、Sabine M.W. van Rossenberg、Reshma Autar、A.Rob P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom、Christina Piperi、P. Anton van der Merwe、Johan Kuiper、Theo J.C. van Berkel、Erik A.L. Biessen

  DOI：10.1016/s0968-0896(00)00224-8

  日期：2001.1

  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.