Epitestosterone glucuronide | 16996-33-1

• 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: Epitestosterone glucuronide
• 英文别名: 17α-hydroxyandrost-4-en-3-one 17-O-glucuronide；epitestosterone-G；epitestosterone 17-O-glucuronide；3-oxoandrost-4-en-17alpha-yl beta-D-glucopyranosiduronic acid；(2S,3S,4S,5R,6R)-6-[[(8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 16996-33-1
• 化学式: C₂₅H₃₆O₈
• 分子量: 464.556
• InChiKey: NIKZPECGCSUSBV-RWUBDERLSA-N

物化性质

• 碰撞截面：
  221.04 Ų [M-H]-; 204.69 Ų [M+H]+

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Epitestosterone glucuronide 、 N-氯-N-吡啶基乙酰肼 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Ion trap MS/MS of intact testosterone and epitestosterone conjugates—Adducts, fragile ions and the advantages of derivatisation

  摘要：

  In ion trap mass spectrometry, fragile ions may fragment under the application of resonance ejection during precursor mass isolation, reducing MS/MS spectral intensity. In this study the steroidal epimers testosterone glucuronide (TG) and epitestosterone glucuronide (EG) have been chosen as a model for exploring whether compound structure is linked to ion trap fragility. Both compounds form multiple adducts by ESI-MS, namely protonation, ammonium and sodium, however, the mass spectrum of EG displays a more intense ammonium adduct peak than TG. [TG + NH4](+), [EG + NH4](+) and [EG + H](+) were found to be fragile ions. To explain the differences in adduct formation and fragility, molecular modelling was employed. Ammonium adduction was localised to the glucuronide ring oxygens and while EG has eight possible adduction sites, only seven were located for TG explaining the increased ammonium adduct abundance with EG. In EG the bond between the steroid and the glucuronide was slightly longer and the oxygen in this bond was more basic than TG. This shows that the EG bond is weaker which may contribute to the fact that [EG + H](+) but not [TG + H](+) is fragile. To investigate whether stability could be restored by chemical means, EG was derivatised with tris(trimethoxyphenyl)phosphonium chloride or methylated on the carboxylic acid and Girard P or methoxylamine on the 3-keto group. Derivatisation of the steroid rather than the glucuronide eliminated fragility and using a charged derivative eliminated adduct formation. This work demonstrates the importance of carefully considering the nature of the derivative and the site of derivatisation. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.01.026
• 作为产物：
  描述：

  α-D-glucuronyl fluoride 、 表睾酮 在 Escherichia coli β-glucuronidase E504G mutant 作用下， 以 aq. phosphate buffer 、 叔丁醇 为溶剂， 反应 48.0h， 生成 Epitestosterone glucuronide
  参考文献：
  名称：

  The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope

  摘要：

  甾体葡萄糖苷酸可以通过使用大肠杆菌葡萄糖苷酸合酶酶快速、方便地在毫克级别上制备，随后通过固相萃取进行纯化。

  DOI：

  10.1039/c4ob00984c

文献信息

• The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope
  作者：Paul Ma、Nicholas Kanizaj、Shu-Ann Chan、David L. Ollis、Malcolm D. McLeod

  DOI：10.1039/c4ob00984c

  日期：——

  Steroid glucuronides can be quickly and conveniently prepared on the milligram scale using theE. coliglucuronylsynthase enzyme followed by purification with solid-phase extraction.

  甾体葡萄糖苷酸可以通过使用大肠杆菌葡萄糖苷酸合酶酶快速、方便地在毫克级别上制备，随后通过固相萃取进行纯化。
• Ion trap MS/MS of intact testosterone and epitestosterone conjugates—Adducts, fragile ions and the advantages of derivatisation
  作者：David A. Cowan、Andrew T. Kicman、Carlos Kubli-Garfias、Helen J. Welchman

  DOI：10.1016/j.steroids.2008.01.026

  日期：2008.7

  In ion trap mass spectrometry, fragile ions may fragment under the application of resonance ejection during precursor mass isolation, reducing MS/MS spectral intensity. In this study the steroidal epimers testosterone glucuronide (TG) and epitestosterone glucuronide (EG) have been chosen as a model for exploring whether compound structure is linked to ion trap fragility. Both compounds form multiple adducts by ESI-MS, namely protonation, ammonium and sodium, however, the mass spectrum of EG displays a more intense ammonium adduct peak than TG. [TG + NH4](+), [EG + NH4](+) and [EG + H](+) were found to be fragile ions. To explain the differences in adduct formation and fragility, molecular modelling was employed. Ammonium adduction was localised to the glucuronide ring oxygens and while EG has eight possible adduction sites, only seven were located for TG explaining the increased ammonium adduct abundance with EG. In EG the bond between the steroid and the glucuronide was slightly longer and the oxygen in this bond was more basic than TG. This shows that the EG bond is weaker which may contribute to the fact that [EG + H](+) but not [TG + H](+) is fragile. To investigate whether stability could be restored by chemical means, EG was derivatised with tris(trimethoxyphenyl)phosphonium chloride or methylated on the carboxylic acid and Girard P or methoxylamine on the 3-keto group. Derivatisation of the steroid rather than the glucuronide eliminated fragility and using a charged derivative eliminated adduct formation. This work demonstrates the importance of carefully considering the nature of the derivative and the site of derivatisation. (C) 2008 Elsevier Inc. All rights reserved.