N-(2-(((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)ethyl)pent-4-enamide | 1030360-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-(((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)ethyl)pent-4-enamide
• CAS: 1030360-72-5
• 化学式: C₂₁H₃₆N₂O₁₂
• 分子量: 508.523
• InChiKey: LFHMQPOQGZCNSM-FLIWFVJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.15
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  216.5
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-(2-(((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)ethyl)pent-4-enamide 、 cytidine 5’-monophosphate-5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-D-galacto-nonulosonic acid 在 Tris-HCl buffer 、 manganese(ll) chloride 作用下， 反应 14.0h， 生成
  参考文献：
  名称：

  Sialoside Analogue Arrays for Rapid Identification of High Affinity Siglec Ligands

  摘要：

  The siglec family of sialic acid binding proteins participates in diverse I cell surface biology that includes regulation of immune cell signaling and the interaction of neuronal cells with glial cells. The weak intrinsic affinity of the natural sialoside ligands has hampered the development of synthetic ligand based probes needed to elucidate their roles in siglec function. In this report, we describe a glycan microarray comprising a library of 9-acyl-substituted sialic acids incorporated into sialosides containing the Neu5Aca2-3Gal and Neu5Aca2-6Gal linkages commonly recognized by the siglecs. The array is demonstrated to exhibit utility for detecting 9-acyl substituents that increase the affinity of siglecs for their ligands. Substituents that increase affinity are anticipated to be useful for the design of high affinity ligand based probes of siglec function.

  DOI：

  10.1021/ja801052g
• 作为产物：
  描述：

  Galβ1-4GlcNAcβ-CH2CH2NH2 、 4-戊烯酐 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以3.12 g的产率得到N-(2-(((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)ethyl)pent-4-enamide
  参考文献：
  名称：

  Sialoside Analogue Arrays for Rapid Identification of High Affinity Siglec Ligands

  摘要：

  The siglec family of sialic acid binding proteins participates in diverse I cell surface biology that includes regulation of immune cell signaling and the interaction of neuronal cells with glial cells. The weak intrinsic affinity of the natural sialoside ligands has hampered the development of synthetic ligand based probes needed to elucidate their roles in siglec function. In this report, we describe a glycan microarray comprising a library of 9-acyl-substituted sialic acids incorporated into sialosides containing the Neu5Aca2-3Gal and Neu5Aca2-6Gal linkages commonly recognized by the siglecs. The array is demonstrated to exhibit utility for detecting 9-acyl substituents that increase the affinity of siglecs for their ligands. Substituents that increase affinity are anticipated to be useful for the design of high affinity ligand based probes of siglec function.

  DOI：

  10.1021/ja801052g