单半乳糖甘油二酯 | 41670-62-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 单半乳糖甘油二酯
• 英文名称: 1,2-O-distearoyl-3-O-(β-D-galactopyranosyl)glycerol
• 英文别名: 1,2-distearoylmonoglactosylglyceride；MGDG；1,2-di-O-stearoyl-3-O-β-D-galactopyranosyl；1,2-Distearoylmonogalactosylglyceride；[2-octadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] octadecanoate
• CAS: 41670-62-6
• 化学式: C₄₅H₈₆O₁₀
• 分子量: 787.172
• InChiKey: DCLTVZLYPPIIID-XMGVTQGESA-N

物化性质

• 沸点：
  826.4±65.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿:甲醇 (1:1): 10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  55
• 可旋转键数：
  41
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  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 、 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 单半乳糖甘油二酯
  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。
• Cholesterol-containing compounds and their use as immunogens against borrelia burgdorferi
  申请人：Ben-Menachem Gil

  公开号：US20060204515A1

  公开（公告）日：2006-09-14

  Unique compounds that can be used for inducing an immune response to Borrelia burgdorferi in a subject by administering a therapeutically effective amount of the glycolipid to the subject. Such administration is particularly useful for preventing or treating Lyme disease in a subject. The compounds(s), and therapeutically acceptable salts thereof, may be formulated into pharmaceutical or immunogenic compositions.

  本发明涉及一种独特的化合物，可通过向受试者施用治疗有效量的糖脂来诱导对伯氏螺旋体的免疫反应。这种治疗特别适用于预防或治疗受试者的莱姆病。这些化合物及其治疗上可接受的盐可以制成药物或免疫原组合物。
• CHOLESTEROL-CONTAINING COMPOUNDS AND THEIR USE AS IMMUNOGENS AGAINST BORRELIA BURGDORFERI
  申请人：Ben-Menachem Gil

  公开号：US20100062023A1

  公开（公告）日：2010-03-11

  Unique compounds that can be used for inducing an immune response to Borrelia burgdorferi in a subject by administering a therapeutically effective amount of the glycolipid to the subject. Such administration is particularly useful for preventing or treating Lyme disease in a subject. The compounds(s), and therapeutically acceptable salts thereof, may be formulated into pharmaceutical or immunogenic compositions.

  本发明涉及一种独特的化合物，可通过向受试者投与治疗有效量的糖脂来诱导免疫反应，从而在受试者中预防或治疗莱姆病。该化合物（及其治疗上可接受的盐）可制成药物或免疫原组合物。
• An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids
  作者：Emiliano Manzo、Maria Letizia Ciavatta、Dario Pagano、Angelo Fontana

  DOI：10.1016/j.tetlet.2011.12.030

  日期：2012.2

  Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.
• CHOLESTEROL-CONTAINING COMPOUNDS AND THEIR USE AS IMMUNOGENS AGAINST BORRELIA BURGDORFERI
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1613641B1

  公开（公告）日：2009-01-14