(S)-N1,N4-bis(3-(((2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-aminosuccinamide | 1354944-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N1,N4-bis(3-(((2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-aminosuccinamide
• CAS: 1354944-97-0
• 化学式: C₃₈H₆₇N₅O₂₄
• 分子量: 977.969
• InChiKey: MJAYQKVVQBYFTG-HDYCSFGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.71
• 重原子数：
  67.0
• 可旋转键数：
  23.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  459.02
• 氢给体数：
  17.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  (S)-N1,N4-bis(3-(((2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-aminosuccinamide 在 sodium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Molecular Design of Fluorescent Labeled Glycosides as Acceptor Substrates for Sialyltransferases

  摘要：

  一系列带有终端N-乙酰乳糖胺（LacNAc）序列的二糖、四糖和六糖的丹酰标记糖苷被合成为α2,6-和α2,3-唾液酸转移酶的受体底物。作为替代设计，通过用烷基链替换LacNAc或乳糖单元，开发了一种带有长间隔链接糖的丹酰标记LacNAc糖苷。此外，我们设计了一种丹酰标记的双抗体LacNAc糖苷，作为N-linked寡糖的模拟物，例如非唾液酸α1-酸性糖蛋白。采用荧光HPLC方法确定了合成的丹酰标记糖苷在唾液酸转移酶转移反应中的动力学参数。对于携带终端LacNAc序列的受体底物，其在不同长度糖链中的催化效率（V_max/K_m）呈现出依赖于糖链长度的下降趋势。此外，在测试的受体底物中，丹酰标记的双抗体LacNAc糖苷对α2,6-和α2,3-唾液酸转移酶显示出最有利的K_m值。

  DOI：

  10.1271/bbb.100505
• 作为产物：
  描述：

  3-aminopropyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (S)-N1,N4-bis(3-(((2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-aminosuccinamide
  参考文献：
  名称：

  Molecular Design of Fluorescent Labeled Glycosides as Acceptor Substrates for Sialyltransferases

  摘要：

  一系列带有终端N-乙酰乳糖胺（LacNAc）序列的二糖、四糖和六糖的丹酰标记糖苷被合成为α2,6-和α2,3-唾液酸转移酶的受体底物。作为替代设计，通过用烷基链替换LacNAc或乳糖单元，开发了一种带有长间隔链接糖的丹酰标记LacNAc糖苷。此外，我们设计了一种丹酰标记的双抗体LacNAc糖苷，作为N-linked寡糖的模拟物，例如非唾液酸α1-酸性糖蛋白。采用荧光HPLC方法确定了合成的丹酰标记糖苷在唾液酸转移酶转移反应中的动力学参数。对于携带终端LacNAc序列的受体底物，其在不同长度糖链中的催化效率（V_max/K_m）呈现出依赖于糖链长度的下降趋势。此外，在测试的受体底物中，丹酰标记的双抗体LacNAc糖苷对α2,6-和α2,3-唾液酸转移酶显示出最有利的K_m值。

  DOI：

  10.1271/bbb.100505

文献信息

• Synthesis of tetravalent LacNAc-glycoclusters as high-affinity cross-linker against Erythrina cristagalli agglutinin
  作者：Makoto Ogata、Yasushi Chuma、Yoshinori Yasumoto、Takashi Onoda、Myco Umemura、Taichi Usui、Enoch Y. Park

  DOI：10.1016/j.bmc.2015.11.026

  日期：2016.1

  Four kinds of tetravalent double-headed glycoclusters [(LacNAc)(4)-DHGs] were designed with linkers of varying lengths consisting of alkanedioic carboxyamido groups (C-6, C-12, C-18 and C-24) between two bi-antennary LacNAc-glycosides. These glycoclusters served as high-affinity cross-linking ligands for the LacNAc-binding lectin Erythrina cristagalli agglutinin (ECA). The binding activity and cross-linking between each ligand and ECA were characterized by a hemagglutination inhibition (HI) assay, isothermal titration calorimetry (ITC), a quantitative precipitation assay and dynamic light scattering (DLS). For the precipitation assay and DLS measurement, the synthesized (LacNAc)(4)-DHGs were found to be capable of binding and precipitating the ECA as multivalent ligands. ITC analysis indicated the binding of (LacNAc)(4)-DHGs was driven by a favorable enthalpy change. Furthermore, the entropy penalty from binding (LacNAc)(4)-DHGs clearly decreased in a spacer length-dependent manner. The binding affinities of flexible (LacNAc)(4)-DHGs (C-18 and C-24) with long spacers were found to be more favorable than those of the clusters having short spacers (C-6 and C-12). These results were supported by molecular dynamics simulations with explicit water molecules for the tetravalent glycoclusters with ECA. We concluded that the subtle modification in the epitope-presenting scaffolds exerts the significant effect in the recognition efficiency involved in the LacNAc moieties by ECA. (C) 2015 Elsevier Ltd. All rights reserved.