WILD20

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: WILD20
• 英文别名: (2S,4S,5R,6R)-5-amino-2-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[(2R,3S,4R,5R,6R)-6-[(E,2S,3R)-2-amino-3-hydroxyicos-4-enoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₅₃H₉₇N₃O₂₈
• 分子量: 1224.36
• InChiKey: RINPOXNCRXGFAV-HLYOVLENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  84
• 可旋转键数：
  35
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  531
• 氢给体数：
  20
• 氢受体数：
  31

反应信息

• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以25%的产率得到
  参考文献：
  名称：

  Preparation and characterization of four new variously deacetylated lysogangliosides, breakdown products of GM1

  摘要：

  Four new deacylated lysogangliosides were obtained through alkaline hydrolysis of either C18 or C20 sphingosine homologues of GM1. By this procedure, both the fatty acids residue and the N-acetyl group of sialic acid were removed to give mono-N-acetyl-lysoGM1 (C18 and C20); the additional loss of the N-acetyl group of the acetylgalactosamine moiety gave de-N-acetyl-lysoGM1 (C18 and C20) with three free amino groups. The structures of four deacetylated lysogangliosides were unambiguously characterized by chemical analysis and H-1 and C-13 NMR spectroscopy as well as by negative ion FABMS. The aim of this study was to isolate pure breakdown products of gangliosides, enabling the evaluation of the mechanism of action of glycosphingolipids through their cleavage and identification of structures of potential pharmacological activity. These new substances were prepared as candidates to influence eicosanoid production and the mechanisms dependent on protein kinase C and phospholipase A2.

  DOI：

  10.1016/0008-6215(93)84132-p

文献信息

• Preparation and characterization of four new variously deacetylated lysogangliosides, breakdown products of GM1
  作者：Giovanni Cavallo、Carlo Iavarone、Ezio Tubaro

  DOI：10.1016/0008-6215(93)84132-p

  日期：1993.10

  Four new deacylated lysogangliosides were obtained through alkaline hydrolysis of either C18 or C20 sphingosine homologues of GM1. By this procedure, both the fatty acids residue and the N-acetyl group of sialic acid were removed to give mono-N-acetyl-lysoGM1 (C18 and C20); the additional loss of the N-acetyl group of the acetylgalactosamine moiety gave de-N-acetyl-lysoGM1 (C18 and C20) with three free amino groups. The structures of four deacetylated lysogangliosides were unambiguously characterized by chemical analysis and H-1 and C-13 NMR spectroscopy as well as by negative ion FABMS. The aim of this study was to isolate pure breakdown products of gangliosides, enabling the evaluation of the mechanism of action of glycosphingolipids through their cleavage and identification of structures of potential pharmacological activity. These new substances were prepared as candidates to influence eicosanoid production and the mechanisms dependent on protein kinase C and phospholipase A2.