1-[2-(β-D-galactopyranos-1-yl)-ethyl]-1H-[1,2,3]-triazole-4-carboxylic acid tetradecylamide

• 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: 1-[2-(β-D-galactopyranos-1-yl)-ethyl]-1H-[1,2,3]-triazole-4-carboxylic acid tetradecylamide
• 英文别名: N-tetradecyl-1-[2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]triazole-4-carboxamide
• 化学式: C₂₅H₄₆N₄O₇
• 分子量: 514.663
• InChiKey: IPHDFAKWIFHEHM-LEKAPFLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  159
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 copper(l) iodide 、 三氟化硼乙醚 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 1-[2-(β-D-galactopyranos-1-yl)-ethyl]-1H-[1,2,3]-triazole-4-carboxylic acid tetradecylamide
  参考文献：
  名称：

  Synthesis of Sugar Arrays in Microtiter Plate

  摘要：

  1,3-Dipolar cycloadditions between azides and alkynes were exploited to attach oligosaccharides to a C-14 hydrocarbon chain that noncovalently binds to the microtiter well surface. Synthesis of sugar arrays was performed on a micromolar scale in situ in the microtiter plate. As a model study, the beta-galactosyllipid 5 was displayed on a 4-mumol scale. Formation of product was confirmed via ESI-MS, and the yield was determined via chemical and biological assays. Several complex carbohydrates (6-16) were also displayed in microtiter plates and successfully screened with various lectins. Moreover, sialyl Lewis x (17) was synthesized via the enzymatic fucosylation of a precursor displayed in the plate. Studies on inhibition of this biotransformation have been carried out, and the IC50 value found for the known inhibitor 20 was consistent with previous studies in solution.

  DOI：

  10.1021/ja020887u

文献信息

• Synthesis of Sugar Arrays in Microtiter Plate
  作者：Fabio Fazio、Marian C. Bryan、Ola Blixt、James C. Paulson、Chi-Huey Wong

  DOI：10.1021/ja020887u

  日期：2002.12.1

  1,3-Dipolar cycloadditions between azides and alkynes were exploited to attach oligosaccharides to a C-14 hydrocarbon chain that noncovalently binds to the microtiter well surface. Synthesis of sugar arrays was performed on a micromolar scale in situ in the microtiter plate. As a model study, the beta-galactosyllipid 5 was displayed on a 4-mumol scale. Formation of product was confirmed via ESI-MS, and the yield was determined via chemical and biological assays. Several complex carbohydrates (6-16) were also displayed in microtiter plates and successfully screened with various lectins. Moreover, sialyl Lewis x (17) was synthesized via the enzymatic fucosylation of a precursor displayed in the plate. Studies on inhibition of this biotransformation have been carried out, and the IC50 value found for the known inhibitor 20 was consistent with previous studies in solution.