O-(o-cresylphospho)tyrosine

• 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: O-(o-cresylphospho)tyrosine
• 英文别名: (2S)-2-amino-3-[4-[hydroxy-(2-methylphenoxy)phosphoryl]oxyphenyl]propanoic acid
• 化学式: C₁₆H₁₈NO₆P
• 分子量: 351.296
• InChiKey: ZFHCILAPKBHJSJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-(2-甲基苯氧基)-7,9-二氧杂-8lambda5-磷杂双环[4.4.0]癸-1,3,5-三烯 8-氧化物 、 L-酪氨酸 反应 15.5h， 生成 O-(o-cresylphospho)tyrosine 、
  参考文献：
  名称：

  Development of diagnostics in the search for an explanation of aerotoxic syndrome

  摘要：

  Aerotoxic syndrome is assumed to be caused by exposure to tricresyl phosphate, an additive in engine lubricants and hydraulic fluids that is activated to the toxic 2-(ortho-cresyl)-4H-1,3,2-benzodioxaphosphoran-2-one (CBDP). Currently, there is no laboratory evidence to support intoxication of airline crew members by CBDP. Our goal was to develop methods for testing in vivo exposure by identifying and characterizing biomarkers. Mass spectrometry was used to study the reaction of CBDP with human albumin, free tyrosine, and human butyrylcholinesterase. Human albumin made a covalent bond with CBDP, adding a mass of 170 amu to Tyr411 to yield the o-cresyl phosphotyrosine derivative. Human butyrylcholinesterase made a covalent bond with CBDP on Ser198 to yield five adducts with added masses of 80, 108, 156, 170, and 186 amu. The most abundant adduct had an added mass of 80 amu from phosphate (HPO(3)), a surprising result given that no pesticide or nerve agent is known to yield phosphorylated serine with an added mass of 80 amu. The next most abundant adduct had an added mass of 170 amu to form o-cresyl phosphoserine. It is concluded that toxic gases or oil mists in cabin air may form adducts on plasma butyrylcholinesterase and albumin, detectable by mass spectrometry. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2010.04.032