(2S,3R,4E)-2-(hexacosanoylamido)-1-(4-O-(3-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl)-β-D-glucopyranosyloxy)-3-hydroxyoctadec-4-ene

• 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: (2S,3R,4E)-2-(hexacosanoylamido)-1-(4-O-(3-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl)-β-D-glucopyranosyloxy)-3-hydroxyoctadec-4-ene
• 英文别名: Isoglobotrihexosylceramide；N-[(E,2S,3R)-1-[(2R,3R,4R,5S,6R)-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-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]hexacosanamide
• 化学式: C₆₂H₁₁₇NO₁₈
• 分子量: 1164.61
• InChiKey: JMENXJYBCQFIRK-KRJDXUSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  81
• 可旋转键数：
  49
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-N-hexacosanylsphingenine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以83%的产率得到(2S,3R,4E)-2-(hexacosanoylamido)-1-(4-O-(3-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl)-β-D-glucopyranosyloxy)-3-hydroxyoctadec-4-ene
  参考文献：
  名称：

  Chemoenzymatic Syntheses of iGb3 and Gb3

  摘要：

  [GRAPHICS]Efficient chemoenzymatic syntheses of iGb3 and Gb3 have been developed. Isoglobotrihexose and globotrihexose were enzymatically synthesized by a three-enzyme system in both solid and solution phases. Then iGb3 and Gb3 were chemically synthesized by coupling of the corresponding trisaccharides with lipid.

  DOI：

  10.1021/ol053070p

文献信息

• A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate
  作者：Janice M. H. Cheng、Emma M. Dangerfield、Mattie S. M. Timmer、Bridget L. Stocker

  DOI：10.1039/c4ob00241e

  日期：——

  Isoglobotrihexosylceramide (iGb3, 1) is an immunomodulatory glycolipid that binds to CD1d and is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells.

  异地三糖脂鞘氨醇（iGb3，1）是一种免疫调节糖脂，它结合到CD1d并呈现给不变天然杀伤T细胞受体（iNKT细胞）的T细胞受体（TCR）。
• Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3)
  作者：Chengfeng Xia、Qingjia Yao、Jens Schümann、Emmanuel Rossy、Wenlan Chen、Lizhi Zhu、Wenpeng Zhang、Gennaro De Libero、Peng George Wang

  DOI：10.1016/j.bmcl.2006.01.040

  日期：2006.4

  Glycoceramides call activate NKT cells by binding with CD1d to produce IFN-gamma, IL-4, and other cytokines. An efficient synthetic pathway for alpha-galactosylceramide (KRN7000) was established by coupling a protected galactose donor to a properly protected ceramide. During the investigation, it was discovered that when the ceramide was protected with benzyl groups, only beta-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced alpha-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Gal alpha 1-3Gal beta 1-4Glc donor with 2-azidosphingosine in high yield. Biological assays on the synthetic KRN7000 and iGb3 were performed using human and murine iNKT cell clones or hybridomas. (C) 2006 Elsevier Ltd. All rights reserved.
• US2006/73118
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemoenzymatic Syntheses of iGb3 and Gb3
  作者：Qingjia Yao、Jing Song、Chengfeng Xia、Wenpeng Zhang、Peng George Wang

  DOI：10.1021/ol053070p

  日期：2006.3.2

  [GRAPHICS]Efficient chemoenzymatic syntheses of iGb3 and Gb3 have been developed. Isoglobotrihexose and globotrihexose were enzymatically synthesized by a three-enzyme system in both solid and solution phases. Then iGb3 and Gb3 were chemically synthesized by coupling of the corresponding trisaccharides with lipid.