12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside | 1277170-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-(12-sulfanyldodecoxy)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 1277170-80-5
• 化学式: C₂₆H₄₉NO₁₁S
• 分子量: 583.741
• InChiKey: IRUGNGIDNXATAJ-AGTZLAJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  188
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 sodium methylate 、 silver perchlorate 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and galectin-binding activities of mercaptododecyl glycosides containing a terminal β-galactosyl group

  摘要：

  Mercaptododecyl glycosides containing a terminal beta-galactosyl group were prepared from D-galactose or from D-lactose via hexa-O-acetyl-lactal (10) as a key intermediate. Interactions of these glycolipids (5 kinds) and galectins (beta-galactoside binding lectins, 6 species) were evaluated by surface plasmon resonance (SPR) method. High binding responses were observed for the lactoside, 2-deoxy-lactoside, and lactosaminide with some galectins (Gal-3, -4, -8), whereas the galactoside and 2,3-dideoxy-lactoside showed low binding activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.049

文献信息

• Synthesis and galectin-binding activities of mercaptododecyl glycosides containing a terminal β-galactosyl group
  作者：Teiichi Murakami、Kyoko Yoshioka、Yukari Sato、Mutsuo Tanaka、Osamu Niwa、Soichi Yabuki

  DOI：10.1016/j.bmcl.2010.12.049

  日期：2011.2

  Mercaptododecyl glycosides containing a terminal beta-galactosyl group were prepared from D-galactose or from D-lactose via hexa-O-acetyl-lactal (10) as a key intermediate. Interactions of these glycolipids (5 kinds) and galectins (beta-galactoside binding lectins, 6 species) were evaluated by surface plasmon resonance (SPR) method. High binding responses were observed for the lactoside, 2-deoxy-lactoside, and lactosaminide with some galectins (Gal-3, -4, -8), whereas the galactoside and 2,3-dideoxy-lactoside showed low binding activities. (C) 2010 Elsevier Ltd. All rights reserved.