5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide | 268539-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[2-[[2-[[2-[[3-(azidomethyl)-5-[[2-oxo-2-[[2-oxo-2-[2-[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyethylamino]ethyl]amino]ethyl]carbamoyl]benzoyl]amino]acetyl]amino]acetyl]amino]ethoxy]oxan-2-yl]methyl acetate
• CAS: 268539-16-8
• 化学式: C₄₉H₆₅N₉O₂₆
• 分子量: 1196.1
• InChiKey: MAOHZRNMZYEWDI-UUQOOMILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  84
• 可旋转键数：
  38
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  436
• 氢给体数：
  6
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以100%的产率得到5-azidomethyl-N,N'-bis<2-O-(α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide
  参考文献：
  名称：

  A comparison of biological and calorimetric analyses of multivalent glycodendrimer ligands for concanavalin A

  摘要：

  The cluster glycoside effect - the observation that multivalent glycosides bind to their polyvalent protein receptors with apparent affinities greater than those that can be rationalized solely on the basis of valency is by now a well established phenomenon. As part of a continuing effort to provide a molecular basis for the cluster glycoside effect, we report here the synthesis of two series of mannosylated dendritic ligands and their performance in a range of competitive and non-competitive binding assays, including hemeagglutination inhibition (HIA), enzyme-linked lectin assays (ELLA) and isothermal titration microcalorimetry (ITC). The first series of ligands contained a semi-rigid glycylglycine spacer and showed no significant performance enhancement in any binding studies. The second series of ligands contained a flexible tetraethylene glycol spacer; these ligands showed marked enhancements at tetravalent and hexavalent levels in both HIA (IC50=3 and <0.8 mu M, respectively) and ITC (K-A=6.2x10(4) and 1.5x10(6) M-1, respectively) studies. In all cases, the thermodynamic parameters of association are consistent with non-specific aggregation rather than enhanced lectin-ligand affinity. This conclusion is reinforced by the lack of enhancements in ligand activity observed in ELLA studies. (C) 2000 Elsevier Science I;td. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00589-3
• 作为产物：
  描述：

  1-O-<2-N-(N-benzyloxycarbonyl glycylglycyl)ethyl>-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide
  参考文献：
  名称：

  A comparison of biological and calorimetric analyses of multivalent glycodendrimer ligands for concanavalin A

  摘要：

  The cluster glycoside effect - the observation that multivalent glycosides bind to their polyvalent protein receptors with apparent affinities greater than those that can be rationalized solely on the basis of valency is by now a well established phenomenon. As part of a continuing effort to provide a molecular basis for the cluster glycoside effect, we report here the synthesis of two series of mannosylated dendritic ligands and their performance in a range of competitive and non-competitive binding assays, including hemeagglutination inhibition (HIA), enzyme-linked lectin assays (ELLA) and isothermal titration microcalorimetry (ITC). The first series of ligands contained a semi-rigid glycylglycine spacer and showed no significant performance enhancement in any binding studies. The second series of ligands contained a flexible tetraethylene glycol spacer; these ligands showed marked enhancements at tetravalent and hexavalent levels in both HIA (IC50=3 and <0.8 mu M, respectively) and ITC (K-A=6.2x10(4) and 1.5x10(6) M-1, respectively) studies. In all cases, the thermodynamic parameters of association are consistent with non-specific aggregation rather than enhanced lectin-ligand affinity. This conclusion is reinforced by the lack of enhancements in ligand activity observed in ELLA studies. (C) 2000 Elsevier Science I;td. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00589-3