17Beta-羟基-4-雄烯-3-酮3-[邻羧基甲基]肟 | 58116-37-3

• 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
• 中文名称: 17Beta-羟基-4-雄烯-3-酮3-[邻羧基甲基]肟
• 英文名称: (Z)-testosterone 3-(O-carboxymethyl)oxime
• 英文别名: testosterone (Z)-O-(carboxymethyl)oxime；Testosterone 3-(O-carboxymethyl)oxime；testosterone-3-CMO；CMO-testosterone；syn-17β-Hydroxy-3-(O-Carboxymethyl)oxyimino-4-androsten；testosterone (E)-3-(O-carboxymethyl)oxime；2-[(Z)-[(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]amino]oxyacetic acid
• CAS: 58116-37-3
• 化学式: C₂₁H₃₁NO₄
• 分子量: 361.481
• InChiKey: VDYLVWGBLQNNAW-VLXQCQHTSA-N

物化性质

• 沸点：
  526.8±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36
• 危险类别码：
  R20/21/22,R40

反应信息

• 作为反应物：
  描述：

  17Beta-羟基-4-雄烯-3-酮3-[邻羧基甲基]肟 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 生成 testosterone-DAP-fluorescin
  参考文献：
  名称：

  The preparation of three fluorescence-labelled derivatives of testosterone

  摘要：

  Three fluorescence-labelled derivatives of testosterone were prepared consisting of the steroid separated from the fluorochrome by a hydrocarbon "bridge". "Bridges" of different lengths (C2 to C7) were used as the length required to avoid steric hindrance effects by the fluorochrome in studies on steroid-protein binding was unknown. The three derivatives prepared were: 17 beta-hydroxy--4-androsten-3-one 3-(O-(N-(2'-mercapto)ethyl)carbamoylmethyl)oxime, 17 beta-hydroxy-4-androsten-3-one 3-(O-(N-(3'-amino)propyl)carbamoylmethyl)oxime and 17 beta-hydroxy-4-androsten-3-one 3-(O(N-(7'-amino)heptyl)carbamoylmethyl)oxime. These were then coupled with either a dansyl or a fluorescein molecule. Overall yields were sufficient and the products immunoreactive with anti-testosterone antiserum.

  DOI：

  10.1016/0039-128x(80)90086-0
• 作为产物：
  描述：

  睾酮 、 羧甲基羟胺半盐酸盐 在 四氢吡咯 作用下， 以 甲醇 为溶剂， 反应 1.08h， 生成 17Beta-羟基-4-雄烯-3-酮3-[邻羧基甲基]肟 、 17Beta-羟基-4-雄烯-3-酮3-[邻羧基甲基]肟
  参考文献：
  名称：

  大肠杆菌葡糖醛酸合成酶的实验和动力学研究：合成葡糖醛酸苷缀合物的工程化酶。

  摘要：

  在许多领域，包括药物开发，运动药物测试和农业残留物的检测，葡萄糖醛酸苷代谢产物的检测和研究都是必不可少的。因此，开发用于合成葡糖醛酸苷缀合物的改进方法是重要的目标。衍生自大肠杆菌β-葡萄糖醛酸苷酶的糖合酶在温和条件下提供了高效，可扩展的一步合成β-葡萄糖醛酸苷的方法。在本文中，我们报告了大肠杆菌的实验和动力学研究葡糖醛酸合成酶，包括受体底物，pH，温度，助溶剂和去污剂的影响，从而为葡糖醛酸苷合成提供了最佳条件。酶动力学还揭示了在葡萄糖醛酸合酶反应中可能同时发生底物和产物抑制，但是可以通过明智地选择受体和供体底物浓度来改善这些作用。进行了临时极性取代基的研究，以改善疏水性甾体受体的水溶性。以这种方式，通过三个步骤实现了甾族代谢物脱氢表雄酮3-β- d-葡萄糖醛酸苷的合成，并且脱氢表雄酮的总产率为86％。

  DOI：

  10.1021/jo101914s

文献信息

• Characteristics of anti-testosterone antisera produced by bovine serum albumin conjugates of 15.ALPHA.- and 15.BETA.-carboxymethyltestosterone: Use of (125I)iodinated tracers.
  作者：Yoshinori MIYAKE、Minoru SHIGETOSHI、Masaharu KOJIMA

  DOI：10.1248/cpb.38.951

  日期：——

  Each testosterone-[125I]iodinated histamine derivative where[125I)iodinated histamines were linked to respective 15α- and 15β-carboxymethyltestosterone (15α-and 15β-CMT), testosterone-3-(O-carboxymethyl)oxime (T-3-CMO) and testosterone-17β-hemisuccinate (T-17-HS) were tested for their usefulness as radiotracers in testosterone immunoassay. In the use of anti-15α- and 15β-CMT antisera produced in rabbits against 15α- and 15β-CMT-bovine serum albumin (BSA) conjugates, the antisera with 15α- and 15β-CMT-[125I]iodinated tracers showed low sensitivity and somewhat low specificity in comparison with those of the antisera with tritiated testosterone (T-3H). On the other hand, the antisear with T-3-CMO-[125I]iodinated tracer showed high sensitivity but low specificity for 5α-dihydrotestosterone(5α-DHT)in comparison with T-3H. The T-17-HS-[125I]iodinated tracer was not bound to the antisera. In the use of anti-15α- and 15β-CMT antisera produced in rabbits by pretreatment with 15α-carboxymethyl-5α-DHT linked to a copolymer of D-glutamic acid and D-lysine followed by immunization with 15α- and 15β-CMT-BSA, the antisera with homologous[125I]iodinated tracer showed high sensitivity and specificity.

  将[125I]碘代组胺与相应的15α-和15β-羧甲基睾酮（15α-和15β-CMT）、睾酮-3-（O-羧甲基）肟（T-3-CMO）和睾酮-17β-半琥珀酸盐（T-17-HS）结合，测试每种睾酮-[125I]碘代组胺衍生物作为睾酮免疫分析中放射性示踪剂的有效性。在用兔产生的抗15α-和15β-CMT抗血清与15α-和15β-CMT-牛血清白蛋白（BSA）结合物结合时，与含氚化睾酮（T-3H）的抗血清相比，含15α-和15β-CMT-[125I]碘代示踪剂的抗血清灵敏度较低，特异性也较低。另一方面，与T-3H相比，含T-3-CMO-[125I]碘代示踪剂的抗血清对5α-二氢睾酮（5α-DHT）的灵敏度高，但特异性低。T-17-HS-[125I]碘代示踪剂不与抗血清结合。在用兔产生的抗
• Design and synthesis of a Mn(III)-porphyrin steroid conjugate used as a new cleavable affinity label: on the road to semi-synthetic catalytic antibodies
  作者：Elodie Girgenti、Rémy Ricoux、Jean-Pierre Mahy

  DOI：10.1016/j.tet.2004.07.057

  日期：2004.10

  We here report the synthesis of a novel porphyrin-steroid conjugate which was designed for the site-specific incorporation of a non-natural heme cofactor at the binding site of an anti-estradiol antibody, in order to get a semi-synthetic catalytic antibody with a monooxygenase-like activity. The general strategy involved a coupling reaction between a testosterone modified by an arm bearing a cleavable disulfide bridge and a meso-tetraarylporphyrin bearing two successive meso-ortho-substituted-phenyl rings, alpha,alpha-5,10-bis-[o-(2-carboxyethyl)carboxamido}phenyl]-15,20-diphenyl-porphyrin. The final porphyrin-steroid conjugate was successfully purified and fully characterized, and was subsequently metalated with manganese acetate. The metalloporphyrin moiety will be used to be coupled with the antibody to generate a new biocatalyst with monooxygenase-like activities. (C) 2004 Elsevier Ltd. All rights reserved.
• Experimental and Kinetic Studies of the <i>Escherichia coli</i> Glucuronylsynthase: An Engineered Enzyme for the Synthesis of Glucuronide Conjugates
  作者：Shane M. Wilkinson、Morgan A. Watson、Anthony C. Willis、Malcolm D. McLeod

  DOI：10.1021/jo101914s

  日期：2011.4.1

  and study of glucuronide metabolites is essential in many fields including pharmaceutical development, sports drug testing, and the detection of agricultural residues. Therefore, the development of improved methods for the synthesis of glucuronide conjugates is an important aim. The glycosynthase derived from E. coli β-glucuronidase provides an efficient, scalable, single-step synthesis of β-glucuronides

  在许多领域，包括药物开发，运动药物测试和农业残留物的检测，葡萄糖醛酸苷代谢产物的检测和研究都是必不可少的。因此，开发用于合成葡糖醛酸苷缀合物的改进方法是重要的目标。衍生自大肠杆菌β-葡萄糖醛酸苷酶的糖合酶在温和条件下提供了高效，可扩展的一步合成β-葡萄糖醛酸苷的方法。在本文中，我们报告了大肠杆菌的实验和动力学研究葡糖醛酸合成酶，包括受体底物，pH，温度，助溶剂和去污剂的影响，从而为葡糖醛酸苷合成提供了最佳条件。酶动力学还揭示了在葡萄糖醛酸合酶反应中可能同时发生底物和产物抑制，但是可以通过明智地选择受体和供体底物浓度来改善这些作用。进行了临时极性取代基的研究，以改善疏水性甾体受体的水溶性。以这种方式，通过三个步骤实现了甾族代谢物脱氢表雄酮3-β- d-葡萄糖醛酸苷的合成，并且脱氢表雄酮的总产率为86％。
• The preparation of three fluorescence-labelled derivatives of testosterone
  作者：Ch. Evrain、K.M. Rajkowski、N. Cittanova、M.F. Jayle

  DOI：10.1016/0039-128x(80)90086-0

  日期：1980.6

  Three fluorescence-labelled derivatives of testosterone were prepared consisting of the steroid separated from the fluorochrome by a hydrocarbon "bridge". "Bridges" of different lengths (C2 to C7) were used as the length required to avoid steric hindrance effects by the fluorochrome in studies on steroid-protein binding was unknown. The three derivatives prepared were: 17 beta-hydroxy--4-androsten-3-one 3-(O-(N-(2'-mercapto)ethyl)carbamoylmethyl)oxime, 17 beta-hydroxy-4-androsten-3-one 3-(O-(N-(3'-amino)propyl)carbamoylmethyl)oxime and 17 beta-hydroxy-4-androsten-3-one 3-(O(N-(7'-amino)heptyl)carbamoylmethyl)oxime. These were then coupled with either a dansyl or a fluorescein molecule. Overall yields were sufficient and the products immunoreactive with anti-testosterone antiserum.