Te-phenyl-L-tellurocysteine

• 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: Te-phenyl-L-tellurocysteine
• 英文别名: (2R)-2-amino-3-phenyltellanylpropanoic acid
• 化学式: C₉H₁₁NO₂Te
• 分子量: 292.792
• InChiKey: ZDVZCEWQJVLHBF-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴苯 在 sodium tetrahydroborate 、 magnesium 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 Te-phenyl-L-tellurocysteine
  参考文献：
  名称：

  硒代胱氨酸和碲代胱氨酸的反应性：衍生物的结构和抗氧化活性

  摘要：

  已经制备了l-硒代胱氨酸（5）和l- tellurocystine（6），并且已经在各种pH值下进行了这些氨基酸的反应，即5和6的氧化。使用过氧化氢作为氧化剂，并在酸性和碱性介质中用过量的5和6处理过氧化氢。化合物5经氧化，得到Se IV和Se VI产物。Selenocysteic酸[HO 3 SECH 2 CH（NH 2）COOH] 9，一种新型的硒VI通过单晶X射线衍射研究对化合物进行了分离和表征。相比之下，l- tellurocystine在被H 2 O 2氧化后可得到Te II和Te IV产物。分离出两性离子有机碲酸（IV）[TeCl 3 CH 2 CH（NH 3）COOH] 13并通过NMR和IR光谱，质谱和元素分析对其进行表征。化合物13在正交晶空间群中结晶。l蛋氨酸胱氨酸，当被NaBH 4还原时产生所需的碲酸酯中间体，将其用溴乙酸捕获。此外，还合成了l和d碲半胱氨酸衍生物，[（RTeCH

  DOI：

  10.1002/chem.201803776

文献信息

• Comparative Study on the Bioactivation Mechanisms and Cytotoxicity of <i>Te</i>-Phenyl-<scp>l</scp>-tellurocysteine, <i>Se</i>-Phenyl-<scp>l</scp>-selenocysteine, and <i>S</i>-Phenyl-<scp>l</scp>-cysteine
  作者：Martijn Rooseboom、Nico P. E. Vermeulen、Fatma Durgut、Jan N. M. Commandeur

  DOI：10.1021/tx020034f

  日期：2002.12.1

  Tellurium compounds are effective antioxidants and chemoprotectors, even more active than their selenium and sulfur analogues. In addition to these properties, some selenium compounds, such as selenocysteine Se-conjugates, possess significant chemopreventive and antitumor activities, and selenol metabolites are considered as active species. In the present study, we have synthesized Te-phenyl-L-tellurocysteine and evaluated its bioactivation and cytotoxicity. The activities of this compound were compared with those of the corresponding selenium and sulfur analogues. Te-Phenyl-L-tellurocysteine is bioactivated into its corresponding tellurol, as detected by GC-MS, by cysteine conjugate beta-lyase and amino acid oxidase, analogously to what has been shown previously for Se-phenyl-L-selenocysteine. The rate of beta-elimination may reflect the bond strength of the corresponding C-S, C-Se, and C-Te bond. Bioactivation of Te-phenyl-L-tellurocysteine and its selenium and sulfur analogues by oxidative enzymes was evaluated by measuring NADPH-dependent activation of hepatic mGST and inhibition of EROD. Te-Phenyl-L-tellurocysteine and Se-phenyl-L-selenocysteine displayed strong and time-dependent mGST activation, while S-phenyl-L-cysteine resulted in no significant activation. Te-Phenyl-L-tellurocysteine was also a strong inhibitor of EROD activity. In addition to EROD inhibition, Te-phenyl-L-tellurocysteine was the strongest inhibitor of several human cytochrome P450 isoenzymes followed by Se-phenyl-L-selenocysteine, while S-phenyl-L-cysteine was the weakest inhibitor. Interestingly, Te-phenyl-L-tellurocysteine selectively inhibited cytochrome P450 1A1 directly, which is, for example, responsible for the activation of several procarcinogens. Preliminary cytotoxicity studies with Te-phenyl-L-tellurocysteine in freshly isolated rat hepatocytes showed a time-dependent depletion of GSH and LDH leakage comparable with the relatively nontoxic drug paracetamol, while the selenium and sulfur analogues were nontoxic toward rat hepatocytes. In conclusion, because the chemopreventive and antitumor activities of selenium compounds are thought to be mediated via their selenol metabolites and tellurium compounds might be even more active than selenium compounds, tellurocysteine Te-conjugates might be an interesting novel class of prodrugs for the formation of biologically active tellurols.
• Reactivity of Selenocystine and Tellurocystine: Structure and Antioxidant Activity of the Derivatives
  作者：Kandhan Satheeshkumar、Saravanan Raju、Harkesh B. Singh、Ray J. Butcher

  DOI：10.1002/chem.201803776

  日期：2018.11.27

  these amino acids, i.e., oxidation of 5 and 6, has been performed at various pH values. Hydrogen peroxide was used as an oxidant and it was treated with 5 and 6 in excess in acidic and basic media. Compound 5, upon oxidation, afforded SeIV and SeVI products. Selenocysteic acid [HO3SeCH2CH(NH2)COOH] 9, a novel SeVI compound, was isolated and characterised by single‐crystal X‐ray diffraction studies. In

  已经制备了l-硒代胱氨酸（5）和l- tellurocystine（6），并且已经在各种pH值下进行了这些氨基酸的反应，即5和6的氧化。使用过氧化氢作为氧化剂，并在酸性和碱性介质中用过量的5和6处理过氧化氢。化合物5经氧化，得到Se IV和Se VI产物。Selenocysteic酸[HO 3 SECH 2 CH（NH 2）COOH] 9，一种新型的硒VI通过单晶X射线衍射研究对化合物进行了分离和表征。相比之下，l- tellurocystine在被H 2 O 2氧化后可得到Te II和Te IV产物。分离出两性离子有机碲酸（IV）[TeCl 3 CH 2 CH（NH 3）COOH] 13并通过NMR和IR光谱，质谱和元素分析对其进行表征。化合物13在正交晶空间群中结晶。l蛋氨酸胱氨酸，当被NaBH 4还原时产生所需的碲酸酯中间体，将其用溴乙酸捕获。此外，还合成了l和d碲半胱氨酸衍生物，[（RTeCH