1,2-di-O-stearoyl-3-O-(β-D-glucopyranosyl)-rac-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: 1,2-di-O-stearoyl-3-O-(β-D-glucopyranosyl)-rac-glycerol
• 英文别名: 1,2-O-distearoyl-3-O-β-D-glucopyranosyl-rac-glycerol；1,2-distearoyl-3-[1'-glucosyl]glycerol；[2-octadecanoyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl] octadecanoate；[2-octadecanoyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] octadecanoate
• 化学式: C₄₅H₈₆O₁₀
• 分子量: 787.172
• InChiKey: DCLTVZLYPPIIID-BOFZLWKYSA-N

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

• 作为反应物：
  描述：

  1,2-di-O-stearoyl-3-O-(β-D-glucopyranosyl)-rac-glycerol 在 2,6-二甲基吡啶 、 双氧水 、 碘 、 potassium acetate 、 溶剂黄146 、 三苯基膦 作用下， 以 丁酮 为溶剂， 生成 1,2-O-distearoyl-3-O-β-[(2',3',4'-tri-O-acetyl)-D-sulfoquinovosyl]-(R/S)-glycerol potassium salt
  参考文献：
  名称：

  [EN] PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS
  [FR] PROCÉDÉ DE SYNTHÈSE DE β-6' SULFOQUINOVOSYL DIACYLGLYCÉROLS

  摘要：

  本发明涉及一种β-6-磺酰基葡糖二酰基甘油的合成方法。具体而言，该方法用于合成化合物1,2-O-二硬脂酸-3-O-(β-磺酰基葡糖基)-R/S-甘油，1,2-O-二硬脂酸-3-O-(β-磺酰基葡糖基)-R-甘油或1,2-O-二硬脂酸-3-O-(β-磺酰基葡糖基)-S-甘油，分别命名为Sulfavant A，Sulfavant R和Sulfavant S。

  公开号：

  WO2022034429A1
• 作为产物：
  描述：

  1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)glycerol 在 4-二甲氨基吡啶 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1,2-di-O-stearoyl-3-O-(β-D-glucopyranosyl)-rac-glycerol
  参考文献：
  名称：

  海洋合成的磺基糖脂的化学合成，一类新的分子佐剂。

  摘要：

  疫苗通过预防传染病和慢性病在保护人类健康中起主要作用。最近，我们报道了1,2-O-二硬脂酰基-3-O-β-d-磺基喹喔基甘油（β-SQDG18），在这里称为磺胺类药物A（1），它在体内和体外显示出作为新型分子佐剂的良好前景。测试。在本手稿中，我们提供了有关制备1的合成策略的完整详细信息，包括对活性的化学决定因素以及我们在研究过程中面临的主要技术障碍的讨论。通过基于三氯乙亚氨酸盐方法学和过乙酸盐糖前体的通用方法，可完成Sulfavant A（1）的合成。最终设计为制备一系列有趣的类似物以进一步进行药理优化和开发提供了可能性，

  DOI：

  10.3390/md15090288

文献信息

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

  DOI：10.1016/j.bmc.2006.10.045

  日期：2007.1

  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 monoglucosyl diacylglycerol analogues and establishes for the glucose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.

  制备具有中等长度的脂肪酸酰基链的单葡糖基甘油二酸酯，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葡糖基二酰基甘油类似物的显着活性，并为葡萄糖系列确定了1,2-二取代和辛酰基链是最大活性的适当结构特征。
• Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase
  作者：Francesca Cateni、Paolo Bonivento、Giuseppe Procida、Marina Zacchigna、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.bmcl.2007.01.019

  日期：2007.4

  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.
• Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides
  作者：Wicharn Janwitayanuchit、Khanit Suwanborirux、Chamnan Patarapanich、Sunibhond Pummangura、Vimolmas Lipipun、Tirayut Vilaivan

  DOI：10.1016/j.phytochem.2003.09.008

  日期：2003.12

  Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.
• Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants
  作者：Emiliano Manzo、Laura Fioretto、Dario Pagano、Genoveffa Nuzzo、Carmela Gallo、Raffaele De Palma、Angelo Fontana

  DOI：10.3390/md15090288

  日期：——

  here named Sulfavant A (1), which shows promising properties as a new molecular adjuvant in in vitro and in vivo tests. In the present manuscript, we provide full details about a synthetic strategy for the preparation of 1, including a discussion of chemical determinants of the activity and the major technical hurdles we faced during the study. Synthesis of Sulfavant A (1) is achieved by a versatile

  疫苗通过预防传染病和慢性病在保护人类健康中起主要作用。最近，我们报道了1,2-O-二硬脂酰基-3-O-β-d-磺基喹喔基甘油（β-SQDG18），在这里称为磺胺类药物A（1），它在体内和体外显示出作为新型分子佐剂的良好前景。测试。在本手稿中，我们提供了有关制备1的合成策略的完整详细信息，包括对活性的化学决定因素以及我们在研究过程中面临的主要技术障碍的讨论。通过基于三氯乙亚氨酸盐方法学和过乙酸盐糖前体的通用方法，可完成Sulfavant A（1）的合成。最终设计为制备一系列有趣的类似物以进一步进行药理优化和开发提供了可能性，