1,3-di-O-octadecanoyl-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: 1,3-di-O-octadecanoyl-2-O-β-D-glucopyranosyl-sn-glycerol
• 英文别名: 1,3-di-O-octadecanoyl-2-O-β-D-glucopyranosyl-glycerol；[3-octadecanoyloxy-2-[(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: BHIUTUXDGHWMNG-PJFMTPSVSA-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：

  1,3-di-O-octadecanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 在 sodium hypochlorite 、 sodium chlorite 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 以43%的产率得到1,3-di-O-octadecanoyl-2-O-β-D-glucuronopyranosyl-sn-glycerol
  参考文献：
  名称：

  与葡萄糖醛酸二酰基甘油相关的阴离子糖脂可抑制蛋白激酶Akt。

  摘要：

  基于2-O-β-D-吡喃葡萄糖基-sn-甘油支架并带有一个或两个不同长度的酰基链的新葡糖醛酸二酰基甘油（GlcADG）类似物已被合成为靶向蛋白激酶Akt的3-磷酸磷脂酰肌醇（PI3P）模拟物。 。使用体外激酶测定法测定了所制备化合物的Akt抑制作用。在人卵巢癌IGROV-1细胞系中测试了该化合物的抗增殖活性，在其中我们发现其中两个可以抑制增殖，并与靶标抑制作用保持一致。

  DOI：

  10.1039/c4ob01602e
• 作为产物：
  描述：

  beta-葡糖基甘油2,3,4,6-四乙酸酯 在 吡啶 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1,3-di-O-octadecanoyl-2-O-β-D-glucopyranosyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• 2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation
  作者：Milind Dangate、Laura Franchini、Fiamma Ronchetti、Takanari Arai、Akira Iida、Harukuni Tokuda、Diego Colombo

  DOI：10.1016/j.bmc.2009.06.064

  日期：2009.8

  New sulfoquinovosyldiacylglycerols derived from 2-O-beta-D-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Glycosyl Glycerols and Related Glycolipids
  作者：René Suhr、Oliver Scheel、Joachim Thiem

  DOI：10.1080/07328309808007465

  日期：1998.8.1

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.
• Anionic glycolipids related to glucuronosyldiacylglycerol inhibit protein kinase Akt
  作者：Maria Vetro、Barbara Costa、Giulia Donvito、Noemi Arrighetti、Laura Cipolla、Paola Perego、Federica Compostella、Fiamma Ronchetti、Diego Colombo

  DOI：10.1039/c4ob01602e

  日期：——

  glucuronosyldiacylglycerol (GlcADG) analogues based on a 2-O-beta-D-glucopyranosyl-sn-glycerol scaffold and carrying one or two acyl chains of different lengths have been synthesized as phosphatidylinositol 3-phosphate (PI3P) mimics targeting the protein kinase Akt. The Akt inhibitory effect of the prepared compounds was assayed using an in vitro kinase assay. The antiproliferative activity of the compounds

  基于2-O-β-D-吡喃葡萄糖基-sn-甘油支架并带有一个或两个不同长度的酰基链的新葡糖醛酸二酰基甘油（GlcADG）类似物已被合成为靶向蛋白激酶Akt的3-磷酸磷脂酰肌醇（PI3P）模拟物。 。使用体外激酶测定法测定了所制备化合物的Akt抑制作用。在人卵巢癌IGROV-1细胞系中测试了该化合物的抗增殖活性，在其中我们发现其中两个可以抑制增殖，并与靶标抑制作用保持一致。