H-Lys(Boc)-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate | 91110-85-9

• 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
• 英文名称: H-Lys(Boc)-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate
• CAS: 91110-85-9
• 化学式: C₅₀H₈₀N₂O₈
• 分子量: 837.194
• InChiKey: XBULTJOREYUXSK-OENYSLKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.61
• 重原子数：
  60.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  143.25
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  H-Lys(Boc)-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate 在 N-甲基吗啉 、 dicyclohexylammonium (2-methyl-1-indolyl)acetate 、 硫氰酸铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 H-(Lys(Boc))2-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate
  参考文献：
  名称：

  Potentiation of the tolerogenicity of benzylpenicilloylated eicosa-L-lysine by conjugation with 4-methoxybenzyl 3.beta.-cholestanyl succinate

  摘要：

  It was previously found that amino acid polymers such as oligolysines bearing haptenic groups in high densities efficiently suppress anti-hapten IgE antibody formation. Such conjugates are strong elicitors of anaphylaxis and therefore may not be used for desensitization of drug allergic patients. Here we report on the synthesis and immunological evaluation of benzylpenicilloylated (BPO) eicosa-L-lysines containing none, one, or two lipophilic p-(hydroxymethyl)benzyl cholestan-3 beta-yl succinate (OSuco) groups. The lipophilic derivatives suppress primary as well as ongoing anti-BPO IgE antibody formation in mice much more efficiently than their hydrophilic counterpart. The lipophilic but not the hydrophilic derivatives form stable micelles in water and suppress the antibody formation according to different cellular mechanisms. The relationship between structure, hydrophobicity, and mode of action is discussed.

  DOI：

  10.1021/jm00377a020
• 作为产物：
  描述：

  对苯二甲醇 在 dicyclohexylammonium (2-methyl-1-indolyl)acetate 、 硫氰酸铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 H-Lys(Boc)-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate
  参考文献：
  名称：

  Potentiation of the tolerogenicity of benzylpenicilloylated eicosa-L-lysine by conjugation with 4-methoxybenzyl 3.beta.-cholestanyl succinate

  摘要：

  It was previously found that amino acid polymers such as oligolysines bearing haptenic groups in high densities efficiently suppress anti-hapten IgE antibody formation. Such conjugates are strong elicitors of anaphylaxis and therefore may not be used for desensitization of drug allergic patients. Here we report on the synthesis and immunological evaluation of benzylpenicilloylated (BPO) eicosa-L-lysines containing none, one, or two lipophilic p-(hydroxymethyl)benzyl cholestan-3 beta-yl succinate (OSuco) groups. The lipophilic derivatives suppress primary as well as ongoing anti-BPO IgE antibody formation in mice much more efficiently than their hydrophilic counterpart. The lipophilic but not the hydrophilic derivatives form stable micelles in water and suppress the antibody formation according to different cellular mechanisms. The relationship between structure, hydrophobicity, and mode of action is discussed.

  DOI：

  10.1021/jm00377a020