3-O-[β-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol | 960204-98-2

• 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-galactopyranosyl-(1->6)-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol
• 英文别名: [(2S)-2-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropyl] hexadecanoate
• CAS: 960204-98-2
• 化学式: C₄₇H₈₈O₁₅
• 分子量: 893.207
• InChiKey: TUUXXJDESDKYDH-QHIDDMOUSA-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''-di-O-benzyl-4'',6''-O-benzylidene-β-D-galactopyranosyl)-(1->6)-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-palmitoyl-sn-glycerol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 以88%的产率得到3-O-[β-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl]-1,2-di-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens

  摘要：

  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.

  DOI：

  10.1016/j.carres.2008.09.028

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.