3-O-[β-D-glucopyranosyl-(1" → 6')-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol | 960204-94-8

• 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: 3-O-[β-D-glucopyranosyl-(1" → 6')-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol
• 英文别名: 3-O-[β-D-glucopyranosyl-(1->6)-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol；3-[beta-D-glucosyl-(1->6)-beta-D-galactosyl]-1,2-dipalmitoyl-sn-glycerol；[(2S)-2-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropyl] hexadecanoate
• CAS: 960204-94-8
• 化学式: C₄₇H₈₈O₁₅
• 分子量: 893.207
• InChiKey: TUUXXJDESDKYDH-GFBMXRCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  62
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3-O-[(2",3",4",6"-tetra-O-benzyl-β-D-glucopyranosyl)-(1" → 6')-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-palmitoyl-sn-glycerol 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙醇 、 环己烯 为溶剂， 反应 6.0h， 以67%的产率得到3-O-[β-D-glucopyranosyl-(1" → 6')-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Chemosynthetic homologues of Mycoplasma pneumoniae β-glycolipid antigens for the diagnosis of mycoplasma infectious diseases

  摘要：

  Mycoplasma pneumoniae expresses beta-glycolipids (beta-GGLs) in cytoplasmic membranes, which possess a unique beta(1 -> 6)-linked disaccharide epitope, which has high potential in biochemical and medicinal applications. In the present study, a series of beta-GGLs homologues with different acyl chains (C12, C14, C16, and C18) were prepared from a common precursor. An ELISA assay using an anti-(beta-GGLs) monoclonal antibody indicated that the synthetic homologues with long acyl chains had greater diagnostic potential in the order C18 > C16 > C14 > C12. Toward a simultaneous detection of natural glycolipids by mass spectrometry (MS), a deuterium-labeled C16 homologue (beta-GGL-C16-d3) was prepared and applied as an internal standard for a high-resolution electrospray ionization MS (ESI-MS) analysis. The ESI-MS analysis was used to identify and quantify acyl homologues (C16/C16, C16/C18, and C18/C18) of beta-GGL-C16 in cultured M. pneumoniae. A beta-GGLs homologue with a 1,2-diacetyl group (C2) was also prepared as a "water soluble" glycolipid homologue and characterized by H-1 NMR spectroscopy. We envisage that each of these chemosynthetic homologues will provide promising approaches to solve medical and biological problems associated with mycoplasma infectious diseases (MIDs). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.12.046

文献信息

• Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens
  作者：Akira Miyachi、Atsushi Miyazaki、Yuko Shingu、Kazuhiro Matsuda、Hirofumi Dohi、Yoshihiro Nishida

  DOI：10.1016/j.carres.2008.09.028

  日期：2009.1

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.