(24ξ)-N-ethyl-24-aminocholest-5-en-3-β-ol | 131932-68-8

• 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
• 英文名称: (24ξ)-N-ethyl-24-aminocholest-5-en-3-β-ol
• CAS: 131932-68-8
• 化学式: C₂₉H₅₁NO
• 分子量: 429.73
• InChiKey: METLADFEAQEOJV-LPFMPMKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  24-oxocholesterol 在 lithium aluminium tetrahydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 88.0h， 生成 (24ξ)-N-ethyl-24-aminocholest-5-en-3-β-ol
  参考文献：
  名称：

  Biosynthetic studies of marine lipids. 31. Evidence for a protonated cyclopropyl intermediate in the biosynthesis of 24-propylidenecholesterol

  摘要：

  The biosynthesis of 24-propylidenecholesterol (11-N) was determined by the use of cell-free extracts from the Chrysophyte alga Chrysoderma mucosa. The biosynthetic sequence was shown to proceed via desmosterol (28-N), 24-methylenecholesterol (29-N), and isofucosterol (30-N) to 24-propylidenecholesterol (11-N). 24-Vinylcholesterol (13-N) was neither a substrate nor a product of the S-adenosylmethionine (SAM)-methyltransferase, nor was it detected in cultures grown in the presence of azasterol inhibitors. Chemical degradation of 24-propylidenecholesterol (11-N) from enzymatic [H-3]SAM methylation of isofucosterol (30-N) provided evidence for the protonated cyclopropane intermediate (27-N). The mechanism involving such an intermediate is consistent with the structures and stereochemical assignments of trace sterols found in this alga. Evidence for the intermediacy of protonated cyclopropanes in the SAM sterol methyl-transfer reactions leading to isofucosterol (30-N), fucosterol (31-N), and 24-methylenecholesterol (29-N) could not be found.

  DOI：

  10.1021/ja00004a047

文献信息

• Biosynthetic studies of marine lipids. 31. Evidence for a protonated cyclopropyl intermediate in the biosynthesis of 24-propylidenecholesterol
  作者：Jose Luis Giner、Carl Djerassi

  DOI：10.1021/ja00004a047

  日期：1991.2

  The biosynthesis of 24-propylidenecholesterol (11-N) was determined by the use of cell-free extracts from the Chrysophyte alga Chrysoderma mucosa. The biosynthetic sequence was shown to proceed via desmosterol (28-N), 24-methylenecholesterol (29-N), and isofucosterol (30-N) to 24-propylidenecholesterol (11-N). 24-Vinylcholesterol (13-N) was neither a substrate nor a product of the S-adenosylmethionine (SAM)-methyltransferase, nor was it detected in cultures grown in the presence of azasterol inhibitors. Chemical degradation of 24-propylidenecholesterol (11-N) from enzymatic [H-3]SAM methylation of isofucosterol (30-N) provided evidence for the protonated cyclopropane intermediate (27-N). The mechanism involving such an intermediate is consistent with the structures and stereochemical assignments of trace sterols found in this alga. Evidence for the intermediacy of protonated cyclopropanes in the SAM sterol methyl-transfer reactions leading to isofucosterol (30-N), fucosterol (31-N), and 24-methylenecholesterol (29-N) could not be found.