3α,11α-dihydroxy-5α-androstan-17-one | 7801-12-9

• 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: 3α,11α-dihydroxy-5α-androstan-17-one
• 英文别名: (3α,5α,11α)-3,11-dihydroxyandrostan-17-one；3α,11α-Dihydroxy-5α-androstan-17-on；11-Hydroxyandrosterone；(3R,5S,8S,9S,10S,11R,13S,14S)-3,11-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 7801-12-9
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: PIXFHVWJOVNKQK-CJWOFWMHSA-N

物化性质

• 熔点：
  235.0 °C
• 溶解度：
  2.55e-04 M

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α,11α-dihydroxy-5α-androstan-17-one 在 Beauveria bassiana KCH 1065 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 3β,11α-dihydroxy-17a-oxa-D-homo-5α-androstan-17-one
  参考文献：
  名称：

  Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

  摘要：

  Beauveria bassiana KCH 1065, as was recently demonstrated, is unusual amongst fungal biocatalysts in that it converts C-19 3-oxo-4-ene and 3 beta-hydroxy-5-ene as well as 3 beta-hydroxy-5 alpha-saturated steroids to 11 alpha-hydroxy ring-D lactones. The Baeyer-Villiger monooxygenase (BVMO) of this strain is distinguished from other enzymes catalyzing BVO of steroidal ketones by the fact that it oxidizes solely substrates with 11 alpha-hydroxyl group. The current study using a series of 5 alpha-saturated steroids (androsterone, 3 alpha-androstanediol and androstanedione) has highlighted that a small change of the steroid structure can result in significant differences of the metabolic fate. It was found that the 3 alpha-stereochemistry of hydroxyl group restricted "normal" binding orientation of the substrate within 11 alpha-hydroxylase and, as a result, androsterone and 3 alpha-androstanediol were converted into a mixture of 7 beta-, 11 alpha- and 7 alpha-hydroxy derivatives. Hydroxylation of androstanedione occurred only at the 11 alpha-position, indicating that the 3-oxo group limits the alternative binding orientation of the substrate within the hydroxylase. Only androstanedione and 3 alpha-androstanediol were metabolized to hydroxylactones. The study uniquely demonstrated preference for oxidation of equatorial (11 alpha-, 7 beta-) hydroxyketones by BVMO from B. bassiana. The time course experiments suggested that the activity of 17 beta-HSD is a factor determining the amount of produced ring-D lactones. The obtained 11 alpha-hydroxylactones underwent further transformations (oxy-red reactions) at C-3. During conversion of androstanedione, a minor dehydrogenation pathway was observed with generation of 11 alpha,17 beta-dihydroxy-5 alpha-androst-1-en-3-one. The introduction of C1-C2 double bond has been recorded in B. bassiana for the first time. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.006
• 作为产物：
  描述：

  11α-hydroxy-5α-androstan-3,17-dione 在 2,3,4,5,6-pentahydroxy-hexanal 、 nicotinamide adenine dinucleotide 、 3α-hydroxysteroid dehydrogenase from Comamonas testosteroni 、 GDH from Bacillus subtilis QB₉₂₈ 、 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 以86 %的产率得到3α,11α-dihydroxy-5α-androstan-17-one
  参考文献：
  名称：

  羟基类固醇脱氢酶催化类固醇中 3-酮的高度区域选择性、化学选择性和对映选择性氢化

  摘要：

  证明了在羟基类固醇脱氢酶 (HSDH) 的催化下，类固醇中的 3-酮基可以高度选择性地氢化为 3-羟基类固醇。 Ct3α-HSDH催化的氢化反应以高产率产生了作为主要对映体纯异构体的3α-羟基类固醇，而Ss3β-HSDH催化体系则以优异的产率产生了3β-羟基类固醇。在两种催化体系中，氢化反应在 3-酮基上进行区域选择性，7-、11-、17-和 20-酮基几乎未反应，并且在 C=C 键和酯基未受攻击的情况下进行化学选择性氢化。我们的HSDH促进的氢化反应具有区域选择性、化学选择性和对映选择性高、收率好、条件温和、底物范围广、适合克级合成等优点。值得注意的是，通过我们的氢化方法，可以轻松、高产地获得脱氢表雄酮、布烯醇酮和阿法沙酮等生物活性分子。

  DOI：

  10.1021/acs.orglett.3c03557

文献信息

• METHOD AND KIT FOR SUPER-HIGH-SENSITIVITY MEASUREMENT OF PROTEIN AND NUCLEIC ACID, AND NOVEL ENZYME SUBSTRATE
  申请人：Ito, Etsuro

  公开号：EP2695948A1

  公开（公告）日：2014-02-12

  Provided is a ultra-high-sensitivity assay in which the assay can be made on a commonly used assay apparatus such as an absorptiometer and a plate reader or with naked eyes. The high-sensitivity assay in which the assay can be made on a commonly used assay apparatus or with naked eyes can be provided by combining an enzyme cycling method using thio-NAD(P) as a coenzyme, a labeling enzyme and a substrate for the labeling enzyme optimally, and by amplifying thio-NAD(P)H, which is a signaling substance, exponentially and then quantifying the thio-NAD(P)H colorimetrically.

  本发明提供了一种超高灵敏度检测方法，该方法可在常用的检测仪器（如吸收仪和平板阅读器）上或用肉眼进行检测。通过优化组合使用硫代-NAD(P)作为辅酶的酶循环方法、标记酶和标记酶底物，并通过指数放大作为信号物质的硫代-NAD(P)H，然后用比色法对硫代-NAD(P)H进行定量，可提供可在常用检测仪器上或用肉眼进行检测的高灵敏度检测方法。
• Ultra-high-sensitive assay of protein and nucleic acid and kit, and novel enzyme substrate
  申请人：Ito Etsuro

  公开号：US11221299B2

  公开（公告）日：2022-01-11

  Provided is a ultra-high-sensitivity assay in which the assay can be made on a commonly used assay apparatus such as an absorptiometer and a plate reader or with naked eyes. The high-sensitivity assay in which the assay can be made on a commonly used assay apparatus or with naked eyes can be provided by combining an enzyme cycling method using thio-NAD(P) as a coenzyme, a labeling enzyme and a substrate for the labeling enzyme optimally, and by amplifying thio-NAD(P)H, which is a signaling substance, exponentially and then quantifying the thio-NAD(P)H colorimetrically.

  本发明提供了一种超高灵敏度检测方法，该方法可在常用的检测仪器（如吸收仪和平板阅读器）上或用肉眼进行检测。通过优化组合使用硫代-NAD(P)作为辅酶的酶循环方法、标记酶和标记酶底物，并通过指数放大作为信号物质的硫代-NAD(P)H，然后用比色法对硫代-NAD(P)H进行定量，可提供可在常用检测仪器上或用肉眼进行检测的高灵敏度检测方法。
• Assays for screening activity of modulators of members of the hydroxy steroid (17-beta) dehydrogenase (HSD17B) family
  申请人：Regeneron Pharmaceuticals, Inc.

  公开号：US11479802B2

  公开（公告）日：2022-10-25

  Screening methods as well as kits for identifying modulators of hydroxysteroid (17-beta) dehydrogenase (HSD17B) family member proteins, such as HSD17B13, are provided. The methods comprise screening molecules for their capacity to modulate the HSD17B family member protein, including inhibiting the HSD17B family member protein, as measured by substrate depletion, product concentration from the HSD17B family member protein substrate conversion or NADH concentration, levels of labeled substrate, luciferin light emission, or combinations thereof. Inhibitors of HSD17B family member proteins identified through the screening methods may be used to treat liver diseases, disorders, or conditions in which the HSD17B family member protein plays a role.

  本发明提供了用于鉴定羟基类固醇（17-beta）脱氢酶（HSD17B）家族成员蛋白（如 HSD17B13）调节剂的筛选方法和试剂盒。这些方法包括筛选分子，以确定其调节 HSD17B 家族成员蛋白的能力，包括抑制 HSD17B 家族成员蛋白的能力，通过底物耗竭、HSD17B 家族成员蛋白底物转化产物浓度或 NADH 浓度、标记底物水平、荧光素发光或其组合来测量。通过筛选方法鉴定的 HSD17B 家族成员蛋白的抑制剂可用于治疗 HSD17B 家族成员蛋白起作用的肝脏疾病、失调或病症。
• Bird, T. Geoffrey C.; Fredericks, Peter M.; Jones, Ewart R. H., Journal of the Chemical Society. Perkin transactions I, 1980, p. 750 - 755
  作者：Bird, T. Geoffrey C.、Fredericks, Peter M.、Jones, Ewart R. H.、Meakins, G. Denis

  DOI：——

  日期：——
• Method and kit for super-high-sensitivity measurement of protein and nucleic acid, and novel enzyme substrate
  申请人：Ito, Etsuro

  公开号：EP2695948B1

  公开（公告）日：2016-12-28