benzyl 2-(7-{N-[1S,3R,4S,5R]-(1,3,4,5-tetraacetoxycyclohexanoyl)glycyl}aminocoumarin-4-yl)acetate | 912840-48-3

• 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: benzyl 2-(7-{N-[1S,3R,4S,5R]-(1,3,4,5-tetraacetoxycyclohexanoyl)glycyl}aminocoumarin-4-yl)acetate
• CAS: 912840-48-3
• 化学式: C₃₅H₃₆N₂O₁₄
• 分子量: 708.676
• InChiKey: HUGIQZOWIHXUBH-DMDVLCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  219.91
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-(7-{N-[1S,3R,4S,5R]-(1,3,4,5-tetraacetoxycyclohexanoyl)glycyl}aminocoumarin-4-yl)acetate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.25h， 生成 2-(7-{N-[1S,3R,4S,5R]-(1,3,4,5-tetraacetoxycyclohexanoyl)glycyl}aminocoumarin-4-yl)acetyl-L-leucine tert-butyl ester
  参考文献：
  名称：

  Hydrophilic photolabelling of glycopeptides from the murine liver–intestine (LI) cadherin recognition domain

  摘要：

  LI-Cadherin is a transmembrane glycoprotein involved in cell adhesion of epithelial cells. Its supposed recognition domain contains the peptide motif AAL and is distinctly hydrophobic. In order to obtain sufficiently soluble model compounds, glycan side chains of T-antigen, (2,6)sialyl T-antigen and sialyl T-N-antigen structure were linked to the serine located in the supposed turn sequence of the LI-cadherin recognition domain. A quinic acid-glycine-7-amino-coumarine (Quiglac) chromophore was constructed in order to enhance the solubility of labelled LI-cadherin (glyco)peptides in water. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.014
• 作为产物：
  描述：

  benzyl 2-(7-aminocoumarin-4-yl)acetate 在 2,4,6-三甲基吡啶 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.33h， 生成 benzyl 2-(7-{N-[1S,3R,4S,5R]-(1,3,4,5-tetraacetoxycyclohexanoyl)glycyl}aminocoumarin-4-yl)acetate
  参考文献：
  名称：

  Hydrophilic photolabelling of glycopeptides from the murine liver–intestine (LI) cadherin recognition domain

  摘要：

  LI-Cadherin is a transmembrane glycoprotein involved in cell adhesion of epithelial cells. Its supposed recognition domain contains the peptide motif AAL and is distinctly hydrophobic. In order to obtain sufficiently soluble model compounds, glycan side chains of T-antigen, (2,6)sialyl T-antigen and sialyl T-N-antigen structure were linked to the serine located in the supposed turn sequence of the LI-cadherin recognition domain. A quinic acid-glycine-7-amino-coumarine (Quiglac) chromophore was constructed in order to enhance the solubility of labelled LI-cadherin (glyco)peptides in water. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.014