24β-Ethyl-9β,19-cyclo-5α-lanost-25-en-3β-ol | 76236-10-7

• 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: 24β-Ethyl-9β,19-cyclo-5α-lanost-25-en-3β-ol
• 英文别名: 24S-ethyl-9β,19-cyclolanost-25-ene-3β-ol；24β-ethyl-25(27)-dehydrocycloartanol；24S/β-ethyl-25-dehydrocycloartanol；(24S)-polysthicol；(1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R,5S)-5-ethyl-6-methylhept-6-en-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
• CAS: 76236-10-7
• 化学式: C₃₂H₅₄O
• 分子量: 454.78
• InChiKey: SCZACXVTRCZQAH-MOLANHOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  24-亚甲基环阿屯醇 、 S-腺苷-L-蛋氨酸 在 sterol methyl transferase 作用下， 生成 24β-Ethyl-9β,19-cyclo-5α-lanost-25-en-3β-ol 、 24(28)E-24-ethylidene cycloartanol 、 24(28)Z-24-ethylidene cycloartanol
  参考文献：
  名称：

  Sterol methyl transferase. Evidence for successive C-methyl transfer reactions generating Δ24(28)- and Δ25(27)-olefins by a single plant enzyme

  摘要：

  The native SMT from Glycine max (soybean) expressed in Escherichia coli cells catalyzes the step-wise conversion of cycloartenol to 24(28)-methylene cycloartanol to a mixture of stereochemically related Delta(24(28))Z-ethylidene-Delta(24(28))E-ethylidene- and Delta(25(27))-24beta-ethylcyclosterols. [27-C-13]Cycloartenol was tested as a substrate to determine the C-25 configuration of the Delta(24(28))-olefin formed during the first C-1-transfer reaction. This substrate yielded (25-R)-[27-C-13]24(28)-methylenecycloartanol. These results are entirely consistent with the observed stereochernistries of pathway specific 24-alkyl sterols found in plants and additionally revealed for the first time that a SMT can sequentially C-methylate the Delta(24)-bond to generate multiple olefins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01550-2

文献信息

• Sterol methyl transferase. Evidence for successive C-methyl transfer reactions generating Δ24(28)- and Δ25(27)-olefins by a single plant enzyme
  作者：Allen L Dennis、W.David Nes

  DOI：10.1016/s0040-4039(02)01550-2

  日期：2002.9

  The native SMT from Glycine max (soybean) expressed in Escherichia coli cells catalyzes the step-wise conversion of cycloartenol to 24(28)-methylene cycloartanol to a mixture of stereochemically related Delta(24(28))Z-ethylidene-Delta(24(28))E-ethylidene- and Delta(25(27))-24beta-ethylcyclosterols. [27-C-13]Cycloartenol was tested as a substrate to determine the C-25 configuration of the Delta(24(28))-olefin formed during the first C-1-transfer reaction. This substrate yielded (25-R)-[27-C-13]24(28)-methylenecycloartanol. These results are entirely consistent with the observed stereochernistries of pathway specific 24-alkyl sterols found in plants and additionally revealed for the first time that a SMT can sequentially C-methylate the Delta(24)-bond to generate multiple olefins. (C) 2002 Elsevier Science Ltd. All rights reserved.