3beta-Hydroxycholest-5-en-26-al | 32557-11-2

• 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: 3beta-Hydroxycholest-5-en-26-al
• 英文别名: (6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptanal
• CAS: 32557-11-2
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: JUGXQEJPWDYOJV-CCDZVGGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3beta-Hydroxycholest-5-en-26-al 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇
  参考文献：
  名称：

  脂肪酶催化的类固醇侧链中立体异构中心在有机溶剂中的酯交换反应：26-羟基胆固醇的情况

  摘要：

  的洋葱假单胞菌（PCL）脂肪酶选择性催化（25S）的酰化的（25R，S）-26羟基胆固醇的异构体1a中，当酯交换反应与乙酸乙烯酯在（氯仿/四氢呋喃的有机溶剂的混合物不可逆地进行）。

  DOI：

  10.1016/s0957-4166(98)00222-5
• 作为产物：
  描述：

  27-去甲-25-氧代胆固醇 在 咪唑 、 高氯酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 生成 3beta-Hydroxycholest-5-en-26-al
  参考文献：
  名称：

  脂肪酶催化的类固醇侧链中立体异构中心在有机溶剂中的酯交换反应：26-羟基胆固醇的情况

  摘要：

  的洋葱假单胞菌（PCL）脂肪酶选择性催化（25S）的酰化的（25R，S）-26羟基胆固醇的异构体1a中，当酯交换反应与乙酸乙烯酯在（氯仿/四氢呋喃的有机溶剂的混合物不可逆地进行）。

  DOI：

  10.1016/s0957-4166(98)00222-5

文献信息

• Functional Redundancy of Steroid C26-monooxygenase Activity in Mycobacterium tuberculosis Revealed by Biochemical and Genetic Analyses
  作者：Jonathan B. Johnston、Hugues Ouellet、Paul R. Ortiz de Montellano

  DOI：10.1074/jbc.m110.161117

  日期：2010.11

  One challenge to the development of new antitubercular drugs is the existence of multiple virulent strains that differ genetically. We and others have recently demonstrated that CYP125A1 is a steroid C-26-monooxygenase that plays a key role in cholesterol catabolism in Mycobacterium tuberculosis CDC1551 but, unexpectedly, not in the M. tuberculosis H37Rv strain. This discrepancy suggests that the H37Rv strain possesses compensatory activities. Here, we examined the roles in cholesterol metabolism of two other cytochrome P450 enzymes, CYP124A1 and CYP142A1. In vitro analysis, including comparisons of the binding affinities and catalytic efficiencies, demonstrated that CYP142A1, but not CYP124A1, can support the growth of H37Rv cells on cholesterol in the absence of cyp125A1. All three enzymes can oxidize the sterol side chain to the carboxylic acid state by sequential oxidation to the alcohol, aldehyde, and acid. Interestingly, CYP125A1 generates oxidized sterols of the (25S)-26-hydroxy configuration, whereas the opposite 25R stereochemistry is obtained with CYP124A1 and CYP142A1. Western blot analysis indicated that CYP124A1 was not detectably expressed in either the H37Rv or CDC1551 strains, whereas CYP142A1 was found in H37Rv but not CDC1551. Genetic complementation of CDC1551 Delta cyp125A1 cells with the cyp124A1 or cyp142A1 genes revealed that the latter can fully rescue the growth defect on cholesterol, whereas cells overexpressing CYP124A1 grow poorly and accumulate cholest-4-en-3-one. Our data clearly establish a functional redundancy in the essential C-26-monooxygenase activity of M. tuberculosis and validate CYP125A1 and CYP142A1 as possible drug targets.
• [EN] CLONING AND CHARACTERIZATION OF A NOVEL HUMAN CYTOCHROME P450, CYP 27C1, AND A HYBRID HOMOLOG FROM DOLLAR I(XENOPUS LAEVIS))<br/>[FR] CLONAGE ET CARACTÉRISATION D'UNE NOUVELLE P450 DE CYTOCHROME HUMAIN, LA CYP 27C1, ET HOMOLOGUE HYBRIDE ISSU DE DOLLAR I(XENOPUS LAEVIS)
  申请人：CYTOCHROMA INC

  公开号：WO2002064765A2

  公开（公告）日：2002-08-22

  The present invention relates to a novel cytochrome P450 protein, human CYP 27C1, and to the nucleic acid molecule comprising a nucleotide sequence encoding same. The invention also relates to species homologs thereto. A human/Xenopus lævis CYP 27C1 hybrid protein and nucleic acid molecule encoding same is also provided by the invention. In addition, the invention relates to vectors comprising the nucleic acid molecules of the invention, host cells and antibodies directed to CYP 27C1 protein and to recombinant methods directed to produce same. Furthermore, the invention relates to diagnostic and therapeutic methods for detecting and treating CYP 27C1-related disorders and to screening methods for identifying modulators, agonists and antagonists of CYP 27C1 expression and activity.
• Lipase-catalyzed resolution of stereogenic centers in steroid side chains by transesterification in organic solvents: the case of a 26-hydroxycholesterol
  作者：Patrizia Ferraboschi、Shahrzad Rezaelahi、Elisa Verza、Enzo Santaniello

  DOI：10.1016/s0957-4166(98)00222-5

  日期：1998.7

  (PCL) lipase selectively catalyzes the acylation of the (25S)-isomer of the (25R,S)-26-hydroxycholesterol 1a when the transesterification is irreversibly carried out with vinyl acetate in a mixture of organic solvents (chloroform/tetrahydrofuran).

  的洋葱假单胞菌（PCL）脂肪酶选择性催化（25S）的酰化的（25R，S）-26羟基胆固醇的异构体1a中，当酯交换反应与乙酸乙烯酯在（氯仿/四氢呋喃的有机溶剂的混合物不可逆地进行）。