undec-10-ynyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 1022083-72-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: undec-10-ynyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-undec-10-ynoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1022083-72-2
• 化学式: C₂₃H₄₀O₁₁
• 分子量: 492.564
• InChiKey: UYDXGLBIVCUXQG-QFAHURJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  undec-10-ynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以100%的产率得到undec-10-ynyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900MHz NMR analysis

  摘要：

  Undee-10-enyl, undec-10-ynyl and 11-azidoundecyl glycoside analogues corresponding to the oligosaccharides of human gangliosides GM3, GM2 and GM1 were synthesized in high yields using glycosyltransferases from Campylobacter jejuni. Due to poor water solubility of the substrates, the reactions were carried out in methanol-water media, which for the first time were shown to be compatible with the C. jejuni alpha-(2 -> 3)-sialyltransferase (CST-06) and beta-(1 -> 4)-N-acetylgalactosaminyltransferase (CJL-30). Bioequivalence of our synthetic analogues and natural gangliosides was examined by binding to Vibrio cholerae toxin and to the B subunit of Escherichia coli heat-labile enterotoxin. This bioequivalence was confirmed by binding mouse and human monoclonal antibodies to GM1 and acute phase sera containing IgM and IgG antibodies to GM1 from patients with the immune-mediated polyneuropathy Guillain-Barre syndrome. The synthesized compounds were analyzed by 1D and 2D 900 MHz NMR spectroscopy. TOCSY and DQF-COSY experiments in combination with C-13-H-1 correlation measurements (HSQC, HMBC) were carried out for primary structural characterization, and a complete assignment of all H-1 and C-13 chemical shifts is presented. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.007

文献信息

• GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900MHz NMR analysis
  作者：Aliaksei V. Pukin、Carel A.G.M. Weijers、Barend van Lagen、Rainer Wechselberger、Bin Sun、Michel Gilbert、Marie-France Karwaski、Dion E.A. Florack、Bart C. Jacobs、Anne P. Tio-Gillen、Alex van Belkum、Hubert P. Endtz、Gerben M. Visser、Han Zuilhof

  DOI：10.1016/j.carres.2008.01.007

  日期：2008.3

  Undee-10-enyl, undec-10-ynyl and 11-azidoundecyl glycoside analogues corresponding to the oligosaccharides of human gangliosides GM3, GM2 and GM1 were synthesized in high yields using glycosyltransferases from Campylobacter jejuni. Due to poor water solubility of the substrates, the reactions were carried out in methanol-water media, which for the first time were shown to be compatible with the C. jejuni alpha-(2 -> 3)-sialyltransferase (CST-06) and beta-(1 -> 4)-N-acetylgalactosaminyltransferase (CJL-30). Bioequivalence of our synthetic analogues and natural gangliosides was examined by binding to Vibrio cholerae toxin and to the B subunit of Escherichia coli heat-labile enterotoxin. This bioequivalence was confirmed by binding mouse and human monoclonal antibodies to GM1 and acute phase sera containing IgM and IgG antibodies to GM1 from patients with the immune-mediated polyneuropathy Guillain-Barre syndrome. The synthesized compounds were analyzed by 1D and 2D 900 MHz NMR spectroscopy. TOCSY and DQF-COSY experiments in combination with C-13-H-1 correlation measurements (HSQC, HMBC) were carried out for primary structural characterization, and a complete assignment of all H-1 and C-13 chemical shifts is presented. (c) 2008 Elsevier Ltd. All rights reserved.