(α-D-galactopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-(β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-hexadecanamido-4-octadecen-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (α-D-galactopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-(β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-hexadecanamido-4-octadecen-1,3-diol
• 英文别名: Galα(1->3)Galβ(1->4)GlcNAcβ(1->3)Galβ(1->4)Glcβ(1->0)Cer；N-[(E,2S,3R)-1-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]hexadecanamide
• 化学式: C₆₆H₁₂₀N₂O₂₈
• 分子量: 1389.68
• InChiKey: UCUBVUCQXROOIJ-WFAREGRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  96
• 可旋转键数：
  46
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  474
• 氢给体数：
  18
• 氢受体数：
  28

反应信息

• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-... 在 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 14.0h， 以98%的产率得到(α-D-galactopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-(β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-hexadecanamido-4-octadecen-1,3-diol
  参考文献：
  名称：

  Total synthesis of the natural antigen involved in the hyperacute rejection response to xenotransplants

  摘要：

  The major glycosphingolipid in pig vascular endothelium is the ceramide pentasaccharide Gal alpha(1 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc beta(1 --> 0)Cer (1), which binds specifically to human anti-Gal antibody and is involved in the hyperacute rejection response in xenotransplantation from pig to man. The synthesis of 1 and its methyl glycoside 2 is described. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0008-6215(00)00145-2

文献信息

• Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc₄βCer
  作者：Abhishek Santra、Yanhong Li、Hai Yu、Teri J. Slack、Peng George Wang、Xi Chen

  DOI：10.1039/c7cc04090c

  日期：——

  chemoenzymatic method for synthesizing glycosphingolipids using α-Gal pentasaccharyl ceramide as an example is reported here. Enzymatic extension of chemically synthesized lactosyl sphingosine using efficient sequential one-pot multienzyme (OPME) reactions allowed glycosylation be carried out in aqueous solution. Facile C18 cartridge-based quick (<30 minutes) purification proctols were established using

  在此报道了以α-Gal戊糖基神经酰胺为例合成糖鞘脂的高效化学酶法。使用有效的顺序一锅多酶（OPME）反应对化学合成的乳糖基鞘氨醇进行酶促延伸，可以在水溶液中进行糖基化。使用最少量的绿色溶剂（CH 3 CN和H 2 O）建立了基于C18弹药筒的快速（少于30分钟）提纯酚。最后一步中的简单酰化反应可分4步形成目标糖基神经酰胺，总收率为57％。
• Total synthesis of the natural antigen involved in the hyperacute rejection response to xenotransplants
  作者：Christian Gege、Willy Kinzy、Richard R. Schmidt

  DOI：10.1016/s0008-6215(00)00145-2

  日期：2000.10

  The major glycosphingolipid in pig vascular endothelium is the ceramide pentasaccharide Gal alpha(1 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc beta(1 --> 0)Cer (1), which binds specifically to human anti-Gal antibody and is involved in the hyperacute rejection response in xenotransplantation from pig to man. The synthesis of 1 and its methyl glycoside 2 is described. (C) 2000 Elsevier Science Ltd. Ail rights reserved.