3-O-butanoyl-2-O-β-D-glucopyranosyl-sn-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-butanoyl-2-O-β-D-glucopyranosyl-sn-glycerol
• 英文别名: [(2R)-3-hydroxy-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] butanoate
• 化学式: C₁₃H₂₄O₉
• 分子量: 324.328
• InChiKey: BPBZBISFVPPIBR-ITBWZIIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 palladium on activated charcoal 吡啶 、 Pseudomonas cepacia lipase 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.25h， 生成 3-O-butanoyl-2-O-β-D-glucopyranosyl-sn-glycerol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol

  摘要：

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

  DOI：

  10.1016/s0968-0896(99)00137-6

文献信息

• A facile lipase catalyzed access to fatty acid monoesters of
  作者：Diego Colombo、Fiamma Ronchetti、Antonio Scala、Ida M. Taino、Lucio Toma

  DOI：10.1016/0957-4166(96)00073-0

  日期：1996.3

  2-O-beta-D-glucopyranosylglycerol was submitted to acylation using Pseudomonas cepacia lipase as catalyst and 2,2,2-trifluoroethyl esters of various long chain carboxylic acids as acyl carriers. Monoacylation was easily accomplished with preferred formation of the (2S)-1-O-acyl derivatives in reactions showing high regio- and diastereoselectivity. (C) 1996 Elsevier Science Ltd
• Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol
  作者：Diego Colombo、Federica Compostella、Fiamma Ronchetti、Antonio Scala、Lucio Toma、Harukuni Tokuda、Hoyoku Nishino

  DOI：10.1016/s0968-0896(99)00137-6

  日期：1999.9

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.