4alpha,14-Dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-ol

• 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: 4alpha,14-Dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-ol
• 英文别名: (3S,4S,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,7,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
• 化学式: C₃₀H₅₀O
• 分子量: 426.7
• InChiKey: MMNYKQIDRZNIKT-YLANKJTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氧气 、 4alpha,14-Dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-ol 、 1-Deoxy-1-(7,8-dimethyl-2,4-dioxidobenzo[g]pteridin-10(5H)-yl)-5-O-phosphonopentitol 生成 4α-Methyl-5α-ergosta-8,14,24(24¹)-trien-3β-ol 、 草氨酸 、 氢(+1)阳离子 、 水 、 FMN
  参考文献：
  名称：

  厚朴叶醇14α-脱甲基酶（CYP51）反义拟南芥显示生长缓慢且寿命长。

  摘要：

  Obtusifoliol14α-脱甲基酶是固醇生物合成中必不可少的固醇14α-脱甲基酶（CYP51）的植物直系同源物。我们准备了CYP51反义拟南芥，以阐明植物中的甾醇和甾类激素的生物合成。从拟南芥表达序列标签（EST）文库中获得拟南芥CYP51 cDNA（AtCYP51），并在酵母羊毛甾醇14α-脱甲基酶（Erg11）缺陷型突变体中检测其功能。与酵母Erg11信号锚肽融合的重组AtCYP51蛋白能够补充erg11突变，从而证实AtCYP51是功能性固醇14α-脱甲基酶。然后，在CaMV35S启动子下，通过在反义方向上携带带有AtCYP51的pBI载体，将AtCYP51用于产生转基因拟南芥。所得的转基因植物的AtCYP51 mRNA的积累减少，内源性tus倍叶醇的量增加。它们在生长早期显示出半矮表型，并且比对照植物具有更长的寿命。这个新发现的表型与以前表征的缺乏油菜素固醇（BR）的菜油甾醇生物合成突变体不同。

  DOI：

  10.1006/bbrc.2001.5122
• 作为产物：
  描述：

  24-methyl-8-lanosten-3β-ol 生成 4alpha,14-Dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-ol
  参考文献：
  名称：

  KATO, TOSHIRO, J. PESTIC. SCI., 1982, 7, N 3, 427-437

  摘要：

  DOI：

文献信息

• Triazole antifungal agents
  申请人：Wu Nian

  公开号：US20100143455A1

  公开（公告）日：2010-06-10

  New triazole antifungal agents having C6S7 or S6C7 bridges are disclosed. These triazoles provide alternatives to existing antifungals in terms of formulation, bioavailability and activity.

  公开了具有C6S7或S6C7桥的新三唑类抗真菌药物。这些三唑类药物在配方、生物利用度和活性方面提供了替代现有抗真菌药物的选择。
• Method for preparing a fatty substance ester and use thereof in pharmaceutics, cosmetics or food industry
  申请人：——

  公开号：US20030195367A1

  公开（公告）日：2003-10-16

  The invention concerns a method for preparing a fatty substance ester, characterised in that it consists in subjecting to an esterification reaction at least a fatty substance with at least an alcohol compound selected from the group consisting of sterols, stanols, 4-methylsterols and their hydrogenated homologous, triterpene alcohols and their hydrogenated homologues, and mixtures thereof, in the presence of at least a solid catalyst selected in the group consisting of lanthanide oxides and the mixtures of said oxides. Said method enables to obtain products particularly suited for use in the field of pharmaceutics, in particular dermatology, cosmetics and special food production (functional food products, medicinal food products and dietetic food products)

  本发明涉及一种制备脂质酯的方法，其特征在于，在存在至少一种固体催化剂的情况下，将至少一种脂肪物质与来自甾醇、甾酮、4-甲基甾醇及其氢化同系物、三萜醇及其氢化同系物以及其混合物中至少一种醇化合物进行酯化反应。该方法能够获得特别适用于制药领域，尤其是皮肤科、化妆品和特殊食品生产（功能性食品、药用食品和饮食食品）的产品。
• Process for the production of fine chemicals
  申请人：Puzio Piotr

  公开号：US20070118916A1

  公开（公告）日：2007-05-24

  The present invention relates to a process for the production of the fine chemical in a microorganism, a plant cell, a plant, a plant tissue or in one or more parts thereof, preferably in plastids. The invention furthermore relates to nucleic acid molecules, polypeptides, nucleic acid constructs, vectors, antibodies, host cells, plant tissue, propagation material, harvested material, plants, microorganisms as well as agricultural compositions and to their use.

  本发明涉及一种在微生物、植物细胞、植物、植物组织或其一部分中生产精细化学品的过程，优选在质体中进行。此外，本发明还涉及核酸分子、多肽、核酸构建物、载体、抗体、宿主细胞、植物组织、繁殖材料、收获材料、植物、微生物以及农业组合物以及它们的用途。
• Functional Cloning of an Arabidopsis thalianacDNA Encoding Cycloeucalenol Cycloisomerase
  作者：Martha A. Lovato、Elizabeth A. Hart、Michael J.R. Segura、José-Luis Giner、Seiichi P.T. Matsuda

  DOI：10.1074/jbc.275.18.13394

  日期：2000.5

  Plants and certain protists use cycloeucalenol cycloisomerase (EC ) to convert pentacyclic cyclopropyl sterols to conventional tetracyclic sterols. We used a novel complementation strategy to clone a cycloeucalenol cycloisomerase cDNA. Expressing an Arabidopsis thaliana cycloartenol synthase cDNA in a yeast lanosterol synthase mutant provided a sterol auxotroph that could be genetically complemented

  植物和某些原生生物使用环桉烯醇环异构酶（EC）将五环环丙基固醇转化为常规的四环固醇。我们使用了一种新型的互补策略来克隆环桉烯醇环异构酶cDNA。在酵母羊毛甾醇合酶突变体中表达拟南芥环戊烯醇合酶cDNA提供了可以与异构酶遗传互补的固醇营养缺陷型。我们用拟南芥酵母表达文库转化了该酵母菌株，并选择了固醇原营养型，从而获得了一种积累了生物合成麦角固醇的菌株。该新型表型由潜在编码36 kDa蛋白的拟南芥cDNA赋予。我们在大肠杆菌中表达了该cDNA（CPI1），并通过气相色谱-质谱法从该菌株中提取了异构化的环桉烯醇体外制成的奥片三醇。该cDNA将可用于获得异源表达的蛋白质用于催化研究和阐明环丙基固醇的体内作用。
• Characterization and catalytic properties of the sterol 14α-demethylase from <i>Mycobacterium tuberculosis</i>
  作者：Aouatef Bellamine、Anil T. Mangla、W. David Nes、Michael R. Waterman

  DOI：10.1073/pnas.96.16.8937

  日期：1999.8.3

  Sterol 14α-demethylase encoded by CYP51 is a mixed-function oxidase involved in sterol synthesis in eukaryotic organisms. Completion of the Mycobacterium tuberculosis genome project revealed that a protein having homology to mammalian 14α-demethylases might be present in this bacterium. Using genomic DNA from mycobacterial strain H ₃₇ Rv, we have established unambiguously that the CYP51-like gene encodes a bacterial sterol 14α-demethylase. Expression of the M. tuberculosis CYP51 gene in Escherichia coli yields a P450, which, when purified to homogeneity, has the predicted molecular mass, ca. 50 kDa on SDS/PAGE, and binds both sterol substrates and azole inhibitors of P450 14α-demethylases. It catalyzes 14α-demethylation of lanosterol, 24,25-dihydrolanosterol, and obtusifoliol to produce the 8,14-dienes stereoselectively as shown by GC/MS and ¹ H NMR analysis. Both flavodoxin and ferredoxin redox systems are able to support this enzymatic activity. Structural requirements of a 14α-methyl group and Δ ⁸⁽⁹⁾ -bond were established by comparing binding of pairs of sterol substrate that differed in a single molecular feature, e.g., cycloartenol paired with lanosterol. These substrate requirements are similar to those established for plant and animal P450 14α-demethylases. From the combination of results, the interrelationships of substrate functional groups within the active site show that oxidative portions of the sterol biosynthetic pathway are present in prokaryotes.

  CYP51编码的类固醇14α-去甲基酶是参与真核生物类固醇合成的混合功能氧化酶。完成结核分枝杆菌基因组项目揭示，可能存在一种与哺乳动物14α-去甲基酶同源的蛋白质。使用结核分枝杆菌H37Rv菌株的基因组DNA，我们已经明确确定CYP51类似基因编码细菌类固醇14α-去甲基酶。在大肠杆菌中表达M. tuberculosis CYP51基因会产生P450，纯化后在SDS/PAGE上显示预测的分子量约为50 kDa，并结合类固醇底物和P450 14α-去甲基酶的唑类抑制剂。它能催化蜡甾醇、24,25-二氢蜡甾醇和钝叶桐酚的14α-去甲基化反应，产生8,14-二烯，经GC/MS和1H NMR分析表明它有立体选择性。类黄酮蛋白和铁蛋白氧化还原系统都能支持这种酶活性。通过比较具有单一分子特征的一对类固醇底物的结合，如环油菜醇与蜡甾醇，确定了14α-甲基和Δ8（9）-键的结构要求。这些底物要求类似于已经确定的植物和动物P450 14α-去甲基酶的要求。从结果的组合来看，底物功能基团在活性位点内的相互关系表明类固醇生物合成途径的氧化部分存在于原核生物中。