(2R,3R,4S,5R,6R)-2-(3-(decanoyloxy)-2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)propoxy)-6-(((4-oxopentanoyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(4-oxopentanoate) | 925223-16-1

• 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: (2R,3R,4S,5R,6R)-2-(3-(decanoyloxy)-2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)propoxy)-6-(((4-oxopentanoyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(4-oxopentanoate)
• CAS: 925223-16-1
• 化学式: C₅₇H₈₈O₁₈
• 分子量: 1061.31
• InChiKey: QZURPUKSZRXXRV-SMNSYDELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.67
• 重原子数：
  75.0
• 可旋转键数：
  44.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  244.54
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(3-(decanoyloxy)-2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)propoxy)-6-(((4-oxopentanoyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(4-oxopentanoate) 在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 生成 [1-decanoyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
  参考文献：
  名称：

  Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase

  摘要：

  Monoglucosyl and monogalactosyl diglycerides (MGDGs) with medium-long length acyl chains, identified as active components in Euphorbiaccae, were synthesized. They were examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. MGDGs with two octanoyl groups at both 1- and 2-positions showed the most potent activity. The stereoselectivity of pancreatic lipase was investigated in vitro where the preference for the 1 position in MGDGs is strictly related to the length of the acyl chains. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.019
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 吡啶 、 4-二甲氨基吡啶 、 calcium sulfate 、 Mucor miehei lipase 、 氢溴酸 、 碘 、 sodium methylate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5R,6R)-2-(3-(decanoyloxy)-2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)propoxy)-6-(((4-oxopentanoyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(4-oxopentanoate)
  参考文献：
  名称：

  Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase

  摘要：

  Monoglucosyl and monogalactosyl diglycerides (MGDGs) with medium-long length acyl chains, identified as active components in Euphorbiaccae, were synthesized. They were examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. MGDGs with two octanoyl groups at both 1- and 2-positions showed the most potent activity. The stereoselectivity of pancreatic lipase was investigated in vitro where the preference for the 1 position in MGDGs is strictly related to the length of the acyl chains. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.019