12-mercaptododecyl-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 1207721-12-7

• 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: 12-mercaptododecyl-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-(12-sulfanyldodecoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1207721-12-7
• 化学式: C₂₄H₄₆O₁₁S
• 分子量: 542.689
• InChiKey: QMFGBEZGNANPPC-ARYMTDNSSA-N

物化性质

• 熔点：
  180 °C
• 沸点：
  746.2±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  180
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  Lactose 在 sodium methylate 、 copper(II) bis(trifluoromethanesulfonate) 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 12-mercaptododecyl-β-D-galactopyranosyl-(1->4)-β-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.