N-(三((beta-吡喃半乳糖基氧基)甲基)甲基)-N(alpha)-(4-(5-胆甾烯-3beta-氧基)丁二酰基)甘氨酰胺 | 91202-79-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: N-(三((beta-吡喃半乳糖基氧基)甲基)甲基)-N(alpha)-(4-(5-胆甾烯-3beta-氧基)丁二酰基)甘氨酰胺
• 中文别名: (3β)-胆甾-5-烯-3-基4-{[2-({1,3-二(β-D-半乳吡喃糖氧基)-2-[(β-D-半乳吡喃糖氧基)甲基]丙烷-2-基}氨基)-2-羰基乙基]氨基}-4-羰基丁酸酯
• 英文名称: N-methyl>-N^α-<4-(5-cholesten-5β-yloxy)succinyl>glycinamide
• 英文别名: N^α-<4-(5-Cholesten-3β-yloxy)succinyl>-N-glycinamid；N-<methyl>-N^α-<4-(5-cholesten-3β-yloxy)succinyl>glycinamide；N-methyl>-N^α-<4-(5-chloesten-3β-yloxy)succinyl>glycinamide；Tgmac；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 4-[[2-[[1,3-bis[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-2-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]propan-2-yl]amino]-2-oxoethyl]amino]-4-oxobutanoate
• CAS: 91202-79-8
• 化学式: C₅₅H₉₂N₂O₂₂
• 分子量: 1133.34
• InChiKey: ISCFDVIOYCQTEH-SXQGXBMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  383
• 氢给体数：
  14
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  胆固醇琥珀酸单酯 在 N-乙基吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 N-(三((beta-吡喃半乳糖基氧基)甲基)甲基)-N(alpha)-(4-(5-胆甾烯-3beta-氧基)丁二酰基)甘氨酰胺
  参考文献：
  名称：

  A water-soluble cholesteryl-containing Tris-galactoside: synthesis, properties, and use in directing lipid-containing particles to the liver

  摘要：

  The synthesis of a trisgalactoside-terminated cholesterol derivative is described. Tris(galactosyloxymethyl)-aminomethane is coupled to cholesterol by using glycyl and succinyl as intermediate hydrophilic spacer moieties. The resulting cholesteryl ester dissolves easily in water, forming monodisperse micelles. When added to dispersions of liposomes or plasma lipoproteins in water, the substance becomes incorporated rapidly into these structures, causing an increase of their buoyant density. Liposomes or low-density lipoproteins, preloaded with the substance, are rapidly cleared from the circulation and taken up by the liver after intravenous injection in rats. This uptake is inhibited by N-acetylgalactosamine but not by N-acetylglucosamine, indicating the specificity of this process.

  DOI：

  10.1021/jm00376a014

文献信息

• Peter, Martin G.; Boldt, Peter C.; Niederstein, Yvonne, Liebigs Annalen der Chemie, 1990, # 9, p. 863 - 869
  作者：Peter, Martin G.、Boldt, Peter C.、Niederstein, Yvonne、Peter-Katalinic, Jasna

  DOI：——

  日期：——
• A water-soluble cholesteryl-containing Tris-galactoside: synthesis, properties, and use in directing lipid-containing particles to the liver
  作者：H. J. M. Kempen、C. Hoes、J. H. Van Boom、H. H. Spanjer、J. De Lange、A. Langendoen、T. J. C. Van Berkel

  DOI：10.1021/jm00376a014

  日期：1984.10

  The synthesis of a trisgalactoside-terminated cholesterol derivative is described. Tris(galactosyloxymethyl)-aminomethane is coupled to cholesterol by using glycyl and succinyl as intermediate hydrophilic spacer moieties. The resulting cholesteryl ester dissolves easily in water, forming monodisperse micelles. When added to dispersions of liposomes or plasma lipoproteins in water, the substance becomes incorporated rapidly into these structures, causing an increase of their buoyant density. Liposomes or low-density lipoproteins, preloaded with the substance, are rapidly cleared from the circulation and taken up by the liver after intravenous injection in rats. This uptake is inhibited by N-acetylgalactosamine but not by N-acetylglucosamine, indicating the specificity of this process.