15β-hydroxyprogesterone

• 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: 15β-hydroxyprogesterone
• 英文别名: 15beta-Hydroxyprogesterone；(8R,9S,10R,13S,14S,15R,17S)-17-acetyl-15-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: LEWIUXKKQXGQRR-XCEZYFHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  15β-hydroxyprogesterone 在 盐酸 、 对甲苯磺酸 作用下， 以 氯仿 、 苯 为溶剂， 生成 5α,17α-Pregn-14-en-3,20-dion
  参考文献：
  名称：

  Hasegawa,H. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 740 - 744

  摘要：

  DOI：
• 作为产物：
  描述：

  progesterone 生成 15β-hydroxyprogesterone
  参考文献：
  名称：

  McAleer et al., Archives of Biochemistry, 1958, vol. 73, p. 127,129

  摘要：

  DOI：

文献信息

• Engineering of CYP106A2 for steroid 9α- and 6β-hydroxylation
  作者：Julia Nikolaus、Kim Thoa Nguyen、Cornelia Virus、Jan L. Riehm、Michael Hutter、Rita Bernhardt

  DOI：10.1016/j.steroids.2017.01.005

  日期：2017.4

  ABSTRACT CYP 106A2 from Bacillus megaterium ATCC 13368 has been described as a 15&bgr;‐hydroxylase showing also minor 11&agr;‐, 9&agr;‐ and 6&bgr;‐hydroxylase activity for progesterone conversion. Previously, mutant proteins with a changed selectivity towards 11&agr;‐OH‐progesterone have already been produced. The challenge of this work was to create mutant proteins with a higher regioselectivity towards

  摘要 来自巨大芽孢杆菌 ATCC 13368 的 CYP 106A2 被描述为 15°-羟化酶，也显示出较小的 11°-、9°-和 6°-羟化酶活性以促进孕酮转化。以前，已经产生了对 11&agr;-OH-孕酮具有改变选择性的突变蛋白。这项工作的挑战是在类固醇分子的第 9 位和第 6 位创建对羟基化具有更高区域选择性的突变蛋白。9&agr;-羟基孕酮具有药学重要性，因为它是生产具有孕激素活性的生理活性物质的有用中间体。从包含通过活性位点残基的定点诱变和饱和诱变组合产生的突变蛋白的文库中选择了 16 种突变蛋白。其中的四种突变蛋白催化孕酮转化为 9&agr;-OH-孕酮作为主要产物。为了进一步优化，进行了定点诱变。将 7 个突变（D217V、A243V、A106T、F165L、T89N、T247V 或 T247W）引入这四种突变蛋白导致了 28 种新变体，这些变体也用于体内孕酮的转化。与野生型
• Structure and stereochemistry of products of hydroxylation of human steroid hormones by a housefly cytochrome P450 (CYP6A1)
  作者：Neil E. Jacobsen、Katalin E. Kövér、Marat B. Murataliev、René Feyereisen、F. Ann Walker

  DOI：10.1002/mrc.1767

  日期：2006.4

  The structure and stereochemistry of nine steroid metabolites isolated in quantities ranging from 0.15 to 1.8 mg were determined using a variety of NMR techniques, including heteronuclear multiple bond correlation (HMBC) using broadband adiabatic 13C pulses and phase‐sensitive data presentation. Testosterone, androstenedione and progesterone were oxidized with housefly cytochrome P450 6A1 enzyme reconstituted

  使用各种 NMR 技术，包括使用宽带绝热 13C 脉冲和相敏数据表示的异核多键相关 (HMBC)，确定了以 0.15 至 1.8 mg 的数量分离的九种类固醇代谢物的结构和立体化学。睾酮、雄烯二酮和孕酮被家蝇细胞色素 P450 6A1 酶氧化，该酶在体外用家蝇 NADPH 细胞色素 P450 还原酶和细胞色素 b5 重组。使用改进的 HMBC 序列以及 2D 异核单量子相关 (HSQC)、COZY 和核 Overhauser 和交换光谱 (NOESY) 在 CD3OD 中的 NMR 分析，结合对 J 耦合的详细分析表明羟基化仅发生在 β 面上2、12 和 15 位的类固醇。版权所有 © 2006 John Wiley & Sons，
• Herzog et al., Journal of Organic Chemistry, 1959, vol. 24, p. 691,694
  作者：Herzog et al.

  DOI：——

  日期：——
• Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture
  作者：Tomasz Janeczko、Alina Świzdor、Jadwiga Dmochowska-Gładysz、Agata Białońska、Zbigniew Ciunik、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.molcatb.2012.05.009

  日期：2012.10

  Dehydroepiandrosterone (DHEA) (10) and its five derivatives: testosterone (1), androstenedione (2), 17 alpha-methyltestosterone (6), progesterone (13) and pregnenolone (14) were subjected to microbial transformation by the filamentous fungus Didymosphaeria igniaria KCH 6670. The predominant metabolism of the incubated 5-ene steroids (10 and 14) occurred through 3 beta-hydroxy-steroid dehydrogenase/5.4-en isomerase pathways resulting in the generation of a 4-en-3-oxo system on ring-A. The transformations of C-19 steroids (1, 2, and 10) included a hydroxylation at 7 alpha position, ketone-alcohol interconversion at C-17 and reduction of the double bond at C-4 and 3-keto group to the 3 beta-alcohol with 5 alpha-stereochemistry at A/B ring. D. igniaria also carried out 6(7)-dehydrogenation and 6,7 beta-epoxidation during transformation of DHEA. Under these conditions transformation of DHEA (10) gave four products: 7 alpha-hydroxyandrost-4-en-3,17-dione (4), 17 beta-hydroxyandrost-4,6-dien-3-one (11), 17 beta-hydroxyandrost-6 beta-epoxy-4-en-3-one (12) and 3 beta,17 beta-dihydroxy-5 alpha-androstane (5). The compounds 11 and 12 are identified as DHEA metabolites for the first time. The transformation of C-21 steroids (13 and 14) led to the mixture of mono-(mainly 11 alpha- and 15 beta-) and dihydroxy- (7 alpha,15 beta-: 14 alpha,15 beta-; 11 alpha,15 beta-; 11 alpha,14 alpha-) products. 7 alpha,15 beta-Dihydroxypregnan-4-en-3,20-dione (18) and 14 alpha,15 beta-dihydroxypregnan-4-en-320-dione (19) were found to be new compounds. The main product of transformation of 17 alpha-methyltestosterone (6) was 12 beta-hydroxy-17 alpha-methyltestosterone (7). The results of these transformations demonstrate the dependence of hydroxylation position on the structure of steroid nucleus. (c) 2012 Elsevier B.V. All rights reserved.
• Microbiological production of 7-and 15-hydroxy-progesterones
  申请人：OLIN MATHIESON

  公开号：US02753290A1

  公开（公告）日：1956-07-03