12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1277170-74-7

• 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)-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,6S)-2-(hydroxymethyl)-6-(12-sulfanyldodecoxy)-3,6-dihydro-2H-pyran-3-yl]oxy]oxane-3,4,5-triol
• CAS: 1277170-74-7
• 化学式: C₂₄H₄₄O₉S
• 分子量: 508.674
• InChiKey: HOPZNBUOAQLDPL-RWQFOSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 碘 、 sodium methylate 、 sodium acetate 、 copper(II) sulfate 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
  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.