N-{2-N-{2-[1,3-di-(O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyloxy)]propanyl}pentane-1,5-diamidyl}octane-1,8-diamide

• 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: N-{2-N-{2-[1,3-di-(O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyloxy)]propanyl}pentane-1,5-diamidyl}octane-1,8-diamide
• 英文别名: N,N'-bis[1,5-bis[1,3-bis[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy]propan-2-ylamino]-1,5-dioxopentan-2-yl]octanediamide
• 化学式: C₁₂₆H₂₁₆N₆O₉₄
• 分子量: 3319.08
• InChiKey: WFHFOEOKLJXIQA-IRCIQSSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -36.6
• 重原子数：
  226
• 可旋转键数：
  77
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  1600
• 氢给体数：
  62
• 氢受体数：
  94

反应信息

• 作为产物：
  描述：

  辛二酸 、 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 N-甲基吗啉 、 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 50.5h， 以94%的产率得到N-{2-N-{2-[1,3-di-(O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyloxy)]propanyl}pentane-1,5-diamidyl}octane-1,8-diamide
  参考文献：
  名称：

  Synthesis of a series of multivalent homo-, and heteroglycosides and their anti-adhesion activities

  摘要：

  Adhesion of leukocytes to endothelium plays an important role in inflammatory diseases. We previously found that the tetravalent lactoside Gu-4 was able to inhibit leukocyte-endothelial cell adhesion significantly and that CD11b was the target of Gu-4 on the surface of leukocytes. In this report, we aimed to explore the relationship between structural characteristics of glycoclusters and anti-adhesion activity. Using selective glycosylation method and convergent strategy, we synthesized a new series of homoglycoclusters and heteroglycoclusters with diverse structures. And the bioactivities of these compounds were assessed by a static state cell-based adhesion assay. We found that when the linked saccharide fragments are the same, the anti-adhesion activities of compounds with flexible linkers were stronger than those with rigid scaffold such as the benzene ring, and the best flexible linker in the tested compounds was L-glutamic acid. When L-glutamic acid was employed as the linker, glycoclusters with four valences, but not other valences, exhibited the most significant anti-adhesion activity; however, no significant differences in anti-adhesion activity were found among the tetravalentglycosides that were made by linking glucose (32), mannose (TMa-4), cellobiose (34), or lactose (Gu-4). Thus, we conclude that a flexible linker with proper length, such as that of L-glutamic acid, and the linking of four saccharide fragments might be the preferable structural characteristics for the glycocluster compounds with potent anti-adhesion activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.011

文献信息

• Synthesis of a series of multivalent homo-, and heteroglycosides and their anti-adhesion activities
  作者：Qing Li、Ting-Ting Yan、Shan Niu、Yue-Tao Zhao、Xiang-Bao Meng、Zhi-Hui Zhao、Zhong-Jun Li

  DOI：10.1016/j.carres.2013.06.011

  日期：2013.9

  Adhesion of leukocytes to endothelium plays an important role in inflammatory diseases. We previously found that the tetravalent lactoside Gu-4 was able to inhibit leukocyte-endothelial cell adhesion significantly and that CD11b was the target of Gu-4 on the surface of leukocytes. In this report, we aimed to explore the relationship between structural characteristics of glycoclusters and anti-adhesion activity. Using selective glycosylation method and convergent strategy, we synthesized a new series of homoglycoclusters and heteroglycoclusters with diverse structures. And the bioactivities of these compounds were assessed by a static state cell-based adhesion assay. We found that when the linked saccharide fragments are the same, the anti-adhesion activities of compounds with flexible linkers were stronger than those with rigid scaffold such as the benzene ring, and the best flexible linker in the tested compounds was L-glutamic acid. When L-glutamic acid was employed as the linker, glycoclusters with four valences, but not other valences, exhibited the most significant anti-adhesion activity; however, no significant differences in anti-adhesion activity were found among the tetravalentglycosides that were made by linking glucose (32), mannose (TMa-4), cellobiose (34), or lactose (Gu-4). Thus, we conclude that a flexible linker with proper length, such as that of L-glutamic acid, and the linking of four saccharide fragments might be the preferable structural characteristics for the glycocluster compounds with potent anti-adhesion activity. (C) 2013 Elsevier Ltd. All rights reserved.