1-O-(β-D-galactopyranosyl)ethylene glycol | 7420-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(β-D-galactopyranosyl)ethylene glycol
• 英文别名: 1-O-β-D-Galactopyranosylaethylenglykol；1-hydroxyethyl-β-D-galactopyranoside；2-Hydroxyethyl beta-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-(2-hydroxyethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 7420-22-6
• 化学式: C₈H₁₆O₇
• 分子量: 224.211
• InChiKey: SMORULFPMBCEPX-DWOUCZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-(β-D-galactopyranosyl)ethylene glycol 、 2,2,2-trifluoroethyl hexanoate 在 Pseudomonas cepacia lipase 、 Celite 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以67%的产率得到1-O-(6-O-hexanoyl-β-D-galactopyranosyl)ethylene glycol
  参考文献：
  名称：

  Synthesis and anti-tumor-promoting activity of glycoglycerolipid analogues lacking the glycerol backbone

  摘要：

  Glycoglycerolipid analogues lacking the glycerol backbone were prepared through a lipase catalyzed transesterification Of beta-D-galactosylethylene glycol. The inhibitory effect of the resultant isomeric hexanoates at the primary alcoholic positions, beta-D-galactosylethylene glycol itself and nonyl beta-D-galactopyranoside, was tested on Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), as a primary screening test for inhibitors of tumor promotion. All the compounds assayed were found to be less active than the reference 2-O-beta-D-galactopyranosylglycerol derivatives, of which they are simplified models, indicating that the anti-tumor-promoting activity is very closely related to the presence of a free hydroxymethylene group on the glycerol-like aglycone moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00543-6
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-2-hydroxyethane 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以100%的产率得到1-O-(β-D-galactopyranosyl)ethylene glycol
  参考文献：
  名称：

  通过使用悬空末端的DNA模型系统对水中的碳水化合物-芳香族化合物进行实验测量。

  摘要：

  蛋白质碳水化合物的识别对于许多生物学过程至关重要。在这种认识中，碳水化合物-芳香族堆积是一种广泛的但了解很少的结构基序。我们第一次描述了碳水化合物-芳香族相互作用对悬挂端DNA模型系统稳定性的贡献的测量。我们观察到几种单糖与苯部分相互作用的能量学上存在明显差异，具体取决于羟基数，立体化学和吡喃糖环中甲基的存在。岩藻糖-苯对是所研究系列中最稳定的（-0.4 Kcal mol（-1）），并且该相互作用与其他与蛋白质芳香族残基（例如Phe-Phe， Phe-Met，或Phe-His。涉及的非共价力似乎是分散力和非常规的氢键，而疏水作用似乎并不驱动相互作用。

  DOI：

  10.1002/chem.200800335

文献信息

• Experimental Measurement of Carbohydrate-Aromatic Stacking in Water by Using a Dangling-Ended DNA Model System
  作者：Juan C. Morales、José J. Reina、Irene Díaz、Anna Aviñó、Pedro M. Nieto、Ramón Eritja

  DOI：10.1002/chem.200800335

  日期：2008.9.8

  fundamental importance for a large number of biological processes; carbohydrate-aromatic stacking is a widespread, but poorly understood, structural motif in this recognition. We describe, for the first time, the measurement of carbohydrate-aromatic interactions from their contribution to the stability of a dangling-ended DNA model system. We observe clear differences in the energetics of the interactions

  蛋白质碳水化合物的识别对于许多生物学过程至关重要。在这种认识中，碳水化合物-芳香族堆积是一种广泛的但了解很少的结构基序。我们第一次描述了碳水化合物-芳香族相互作用对悬挂端DNA模型系统稳定性的贡献的测量。我们观察到几种单糖与苯部分相互作用的能量学上存在明显差异，具体取决于羟基数，立体化学和吡喃糖环中甲基的存在。岩藻糖-苯对是所研究系列中最稳定的（-0.4 Kcal mol（-1）），并且该相互作用与其他与蛋白质芳香族残基（例如Phe-Phe， Phe-Met，或Phe-His。涉及的非共价力似乎是分散力和非常规的氢键，而疏水作用似乎并不驱动相互作用。
• Synthesis and anti-tumor-promoting activity of glycoglycerolipid analogues lacking the glycerol backbone
  作者：Diego Colombo、Fiamma Ronchetti、Antonio Scala、Lucio Toma、Harukuni Tokuda、Hoyoku Nishino

  DOI：10.1016/s0968-0896(02)00543-6

  日期：2003.3

  Glycoglycerolipid analogues lacking the glycerol backbone were prepared through a lipase catalyzed transesterification Of beta-D-galactosylethylene glycol. The inhibitory effect of the resultant isomeric hexanoates at the primary alcoholic positions, beta-D-galactosylethylene glycol itself and nonyl beta-D-galactopyranoside, was tested on Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), as a primary screening test for inhibitors of tumor promotion. All the compounds assayed were found to be less active than the reference 2-O-beta-D-galactopyranosylglycerol derivatives, of which they are simplified models, indicating that the anti-tumor-promoting activity is very closely related to the presence of a free hydroxymethylene group on the glycerol-like aglycone moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.