3-O-(2',3',4',6'-tetra-O-levulinoyl-β-D-galactopyranosyl)glycerol | 935534-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 3-O-(2',3',4',6'-tetra-O-levulinoyl-β-D-galactopyranosyl)glycerol
• 英文别名: [(2R,3S,4S,5R,6R)-6-(2,3-dihydroxypropoxy)-3,4,5-tris(4-oxopentanoyloxy)oxan-2-yl]methyl 4-oxopentanoate
• CAS: 935534-69-3
• 化学式: C₂₉H₄₂O₁₆
• 分子量: 646.643
• InChiKey: IJXGOWZZHGEFIL-WNBLPLDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  45
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  232
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-O-(2',3',4',6'-tetra-O-levulinoyl-β-D-galactopyranosyl)glycerol 在 吡啶 、 4-二甲氨基吡啶 、 Mucor miehei lipase 、 一水合肼 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-O-decanoyl-2-O-linolenoyl-3-O-(β-D-galactopyranosyl)glycerol
  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：

  1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose 在 吡啶 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 3-O-(2',3',4',6'-tetra-O-levulinoyl-β-D-galactopyranosyl)glycerol
  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

文献信息

• Chemoenzymatic synthesis and antimicrobial activity evaluation of monogalactosyl diglycerides
  作者：Francesca Cateni、Paolo Bonivento、Giuseppe Procida、Marina Zacchigna、Luciana Gabrielli Favretto、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.ejmech.2007.03.012

  日期：2008.1

  examined for antimicrobial activity against Gram positive, Gram negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monogalactosyl diacylglycerol analogues and establishes for the galactose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.

  制备具有中等至长脂肪酸酰基链的单半乳糖甘油二酯，并检查其对革兰氏阳性，革兰氏阴性细菌和真菌的抗菌活性。对它们的体外抗菌活性的研究证实了某些单半乳糖基二酰基甘油类似物的显着活性，并为半乳糖系列确定了1,2-二取代基和辛酰基链是最大活性的适当结构特征。