N-(2-hydroxyethylthioethyl)-L-valine | 190187-17-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-hydroxyethylthioethyl)-L-valine
• 英文别名: N-(HETE)Val；Hydroxyethylthioethyl-valine；(2S)-2-[2-(2-hydroxyethylsulfanyl)ethylamino]-3-methylbutanoic acid
• CAS: 190187-17-8
• 化学式: C₉H₁₉NO₃S
• 分子量: 221.321
• InChiKey: FTCZYWZWXXVQMS-QMMMGPOBSA-N

物化性质

• 熔点：
  209-212 °C (decomp)
• 沸点：
  400.7±35.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  94.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五氟苯基硫代异氰酸酯 、 N-(2-hydroxyethylthioethyl)-L-valine 在 碳酸氢钠 作用下， 以 丙醇 为溶剂， 反应 1.0h， 生成 1-(2-Hydroxyethylthioethyl)-5-isopropyl-3-pentafluorophenyl-2-thiohydantoin
  参考文献：
  名称：

  Biological fate of sulphur mustard: identification of valine and histidine adducts in haemoglobin from casualties of sulphur mustard poisoning

  摘要：

  1. Analytical methods were developed for the detection of N-terminal valine and histidine adducts in haemoglobin alkylated with sulphur mustard.2. N-(2-hydroxyethylthioethyl)-N-terminal valine was selectively cleaved from globin with the Edman reagent pentafluorophenyl isothiocyanate. The resulting thiohydantoin derivative was analysed by high resolution gc-ms using negative ion chemical ionization. An alternative procedure, involving acid hydrolysis of globin to its constituent amino acids and conversion of the adduct to its di-TBDMS derivative, was less sensitive.3. N-(2-hydroxyethylthioethyl)histidine was analysed, after acid hydrolysis of globin, as its fluorenylmethyloxycarbonyl derivative by Ic-ms-ms using electrospray ionisation and selected reaction monitoring.4. N-(2-hydroxyethylthioethyl)valine and (2-hydroxyethpylthioethyl)histidine were detected in globin isolated from a rat treated percutaneously with sulphur mustard, and in globin from five blood samples collected from human casualties of sulphur mustard poisoning. The adducts are proposed as biological markers of sulphur mustard poisoning, in addition to urinary metabolites and DNA adducts.

  DOI：

  10.1080/004982597240460
• 作为产物：
  描述：

  2-羟基乙基 2-氯乙基硫醚 、 L-缬氨酸 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 以70%的产率得到N-(2-hydroxyethylthioethyl)-L-valine
  参考文献：
  名称：

  Synthesis, Characterization and Mass Spectrometric Analysis of Cysteine and Valine Adducts of Sulphur Mustard

  摘要：

  The synthetic standards for cysteine and valine adducts of sulphur mustard have been synthesized using 2-(2-chloroethylthio) ethanol (half-. mustard). These adducts have been recognized as biomarkers for exposure to sulphur mustard. The adducts have been fully characterized using H-1 and C-13 NMR spectroscopy and mass spectrometric techniques.

  DOI：

  10.1080/10426500307916