cholesteryl 6-O-oleoyl-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl 6-O-oleoyl-β-D-galactopyranoside
• 英文别名: cholesteryl 6-O-oleyl-β-D-galactopyranoside；C18:1-ACGal；cholesteryl 6-O-oleoyl-beta-D-galactoside；[(2R,3R,4S,5R,6R)-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-octadec-9-enoate
• 化学式: C₅₁H₈₈O₇
• 分子量: 813.256
• InChiKey: DDMRUBMQFNAWDK-XOOGFWQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  58
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 吡啶 、 甲醇 、 sodium methylate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 43.0h， 生成 cholesteryl 6-O-oleoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Facile Synthesis of a Library of Lyme Disease Glycolipid Antigens

  摘要：

  A library of one of the two Lyme disease antigens, BbGL1, has been synthesized in four steps from D-galactose using BF3-promoted glycosylation of the peracetate to introduce the cholesteryl beta-glycoside and TBTU-promoted esterification to add a range of fatty acids regioselectively at O-6 of D-galactose in good yield.

  DOI：

  10.1021/ol301697c

文献信息

• Chemoenzymatic Synthesis of a Glycolipid Library and Elucidation of the Antigenic Epitope for Construction of a Vaccine Against Lyme Disease
  作者：Gunthard Stübs、Bernd Rupp、Ralf R. Schumann、Nicolas W. J. Schröder、Jörg Rademann

  DOI：10.1002/chem.200902205

  日期：2010.3.15

  prevalent antigen frequently recognized by antibodies in late‐stage LD. Here we report a convenient route for the chemical synthesis of ACGal by employing a combination of chemical synthesis steps with enzymatic transformations. This synthesized molecule was compared with bacterial extracts by immunoblots with patient sera, confirming the preserved antigenicity. Next, a glycolipid library derived from

  莱姆病（LD）是欧洲，北美和亚洲最常见的壁虱传播疾病。LD的病原体是Borrelia burgdorferi sensu lato组的螺旋体，其脂质含量为干重的25–30％。主要糖脂胆固醇6- ö酰基-β- d -galactopyranoside（ACGal），存在于博氏疏螺旋狭义，B. afzelii，和B. garinii，是一种特异且高度流行的抗原，经常被晚期LD的抗体识别。在这里，我们报告了通过化学合成步骤与酶促转化相结合的化学合成ACGal的便捷途径。通过用患者血清进行免疫印迹将该合成的分子与细菌提取物进行比较，确认了保留的抗原性。接下来，设计并合成了衍生自具有脂肪酰基部分变化的天然分子的糖脂文库和其中胆固醇已被取代的衍生物。化学结构通过1D和2D NMR光谱法和质谱法确认。将天然和合成的糖脂用于免疫印迹，以确定患者血清中抗体识别的表位。通过这种方法，我们可以证明半乳糖 胆固醇
• Synthesis of two glycolipid antigens of the causative agent of Lyme disease
  作者：Vince Pozsgay、Joanna Kubler-Kielb、Bruce Coxon、Göran Ekborg

  DOI：10.1016/j.tet.2005.08.053

  日期：2005.10

  As a prelude to development of a human vaccine against Lyme disease, the first chemical synthesis of glycolipid antigens of Borrelia burkholderi is reported. First, cholesteryl β-d-galactopyranoside was synthesized and was converted to partially protected congeners having the HO-6 group of the galactose moiety unprotected. Treatment of these intermediates with palmitic and oleic acid, respectively

  作为开发针对莱姆病的人类疫苗的前奏，据报道伯氏疏螺旋体的糖脂抗原的第一化学合成。首先，合成胆固醇基β-d-吡喃半乳糖苷，并将其转化为半乳糖部分的HO-6基团未保护的部分保护的同类物。在脱水条件下分别用棕榈酸和油酸处理这些中间体，然后除去保护基，得到与从伯克霍尔德氏菌分离的糖脂相同的胆固醇基6 - O-棕榈酰基/油酰基-β-d-吡喃半乳糖苷。
• Facile Synthesis of a Library of Lyme Disease Glycolipid Antigens
  作者：Jean-d’Amour K. Twibanire、Raha Parvizi Omran、T. Bruce Grindley

  DOI：10.1021/ol301697c

  日期：2012.8.3

  A library of one of the two Lyme disease antigens, BbGL1, has been synthesized in four steps from D-galactose using BF3-promoted glycosylation of the peracetate to introduce the cholesteryl beta-glycoside and TBTU-promoted esterification to add a range of fatty acids regioselectively at O-6 of D-galactose in good yield.
• Vudhgiri, Srikanth; Dhevendar, Koude; Misra, Sunil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2018, p. 91 - 97
  作者：Vudhgiri, Srikanth、Dhevendar, Koude、Misra, Sunil、Prasad、Jala, Ram Chandra Reddy

  DOI：——

  日期：——