6-(N-trifluoroacetylamino)hexyl α-D-mannopyranoside | 129460-87-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(N-trifluoroacetylamino)hexyl α-D-mannopyranoside
• 英文别名: 6-(trifluoroacetylamino)hexyl-α-D-mannopyranoside；6-(trifluoroacetamido)hexyl α-D-mannopyranoside
• CAS: 129460-87-3
• 化学式: C₁₄H₂₄F₃NO₇
• 分子量: 375.342
• InChiKey: YHJSFDZWLXUCGZ-GCHJQGSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  128.48
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-(N-trifluoroacetylamino)hexyl α-D-mannopyranoside 在 水 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 27.0h， 生成 6-(tert-butoxycarbonylamino)hexyl α-D-mannopyranoside
  参考文献：
  名称：

  含有末端D-甘露糖6-磷酸残基的支链糖肽衍生物的合成。

  摘要：

  通过将6-氨基己基6-O- [双（2,2,2-三氯乙氧基）亚膦酰基]-α-D-甘露吡喃糖苷与N-乙酰基-L-偶合制备结合了两个D-甘露糖6-磷酸残基的支链糖肽衍生物酪氨酰基-L-天冬氨酸-酰基二-L-丙氨酸，然后还原性脱保护磷酸基团。

  DOI：

  10.1016/0008-6215(90)84295-6
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 sodium methylate 、 四氯化锡 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 6-(N-trifluoroacetylamino)hexyl α-D-mannopyranoside
  参考文献：
  名称：

  含有末端D-甘露糖6-磷酸残基的支链糖肽衍生物的合成。

  摘要：

  通过将6-氨基己基6-O- [双（2,2,2-三氯乙氧基）亚膦酰基]-α-D-甘露吡喃糖苷与N-乙酰基-L-偶合制备结合了两个D-甘露糖6-磷酸残基的支链糖肽衍生物酪氨酰基-L-天冬氨酸-酰基二-L-丙氨酸，然后还原性脱保护磷酸基团。

  DOI：

  10.1016/0008-6215(90)84295-6

文献信息

• A facile synthesis of 2-O-(α-
  作者：Reiko T. Lee、Yuan C. Lee

  DOI：10.1016/0008-6215(95)00047-w

  日期：1995.7
• Binding specificity of d-mannose 6-phosphate receptor of rabbit alveolar macrophages
  作者：Hiroshi Tomoda、Yukihide Ohsumi、Yoshitaka Ichikawa、Om P. Srivastava、Yasuo Kishimoto、Yuan Chuan Lee

  DOI：10.1016/s0008-6215(00)90596-2

  日期：1991.6

  The existence of terminal D-mannosyl 6-phosphate groups (Man-6-P) was required (for an inhibitor) to exert a strong inhibitory potency against the binding of bovine serum albumin (BSA) conjugated with 17 molecules of penta-D-mannose 6-phosphate [(M5P)17-BSA] to the Man-6-P receptor in rabbit alveolar macrophages. In addition, the underlying oligosaccharide structures, such as linkage mode between the nonreducing sugar group and the penultimate sugar residue, and the length of sugar chain also affected the inhibitory potency in this system. In general, the oligosaccharides with an alpha-(1 --> 2)-linked Man-6-P unit gave stronger inhibitory potencies than those with an alpha-(1 --> 3)- or alpha-(1 --> 6)-linked Man-6-P unit. Trisaccharides containing a terminal Man-6-P group were more potent inhibitors than disaccharides. A synthetic, branched, and divalent ligand, which does not have a penultimate sugar residue, gave about the same level of inhibitory potency as Man-6-P itself. The "cluster effect" was observed in this system, i.e., as the number of Man-6-P units conjugated to BSA [(Man-6-P)5.5, 8, and 46-BSA] increased, the stronger inhibitory potencies were observed with decreasing I50 values of 1.93, 1.36, and 0.0345-mu-M, respectively. Synthetic divalent oligosaccharides also showed higher inhibitory potencies than the corresponding monovalent oligosaccharides.