S-cyclohexylmethyl mercapturic acid

• 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: S-cyclohexylmethyl mercapturic acid
• 英文别名: (2R)-2-acetamido-3-(cyclohexylmethylsulfanyl)propanoic acid
• 化学式: C₁₂H₂₁NO₃S
• 分子量: 259.37
• InChiKey: FTKHGTJIGOLZNF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 溴甲基环己烷 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以73%的产率得到S-cyclohexylmethyl mercapturic acid
  参考文献：
  名称：

  An improved method for cysteine alkylation

  摘要：

  An improved method for the synthesis of S-alkylated cysteine derivatives with branched alkyl chains is reported. These compounds can be obtained in good yield and high purity by refluxing the cysteine thiol with the appropriate alkyl bromide in a solution of sodium ethoxide in ethanol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00098-3

文献信息

• Development of a Class-Selective Enzyme-Linked Immunosorbent Assay for Mercapturic Acids in Human Urine
  作者：Christian Lohse、Lynn L. Jaeger、Norbert Staimer、Jim R. Sanborn、A. Daniel Jones、József Langó、Shirley J. Gee、Bruce D. Hammock

  DOI：10.1021/jf000621b

  日期：2000.12.1

  Epidemiological and toxicological studies often require the analysis of large numbers of samples for biological markers of exposure. The goal of this work was- to develop a class-selective ELISA to detect groups of structurally closely related mercapturic acids with small nonpolar S-substituents. An assay was developed with strong recognition for mercapturates including S-benzylmercapturic acid (IC50 = 0.018 mu mol/L), S-n-hexylmercapturic acid (IC50 = 0.021 mu mol/L), S-phenylmercapturic acid (IC50 = 0.024 mu mol/L), and S-cyclohexylmethylmercapturic acid (IC50 = 0.042 mu mol/L). The same assay also showed weaker recognition for S-(1-hydroxynaphthal-2-yl)mercapturic acid and S-allylmercapturic acid (IC50 = 1.1 and 1.7 mu mol/L, respectively). Subtle modifications to the hapten linker structure of the coating antigen proved to have a strong impact on the selectivity and the specificity of the assay. A slightly modified assay showed high recognition for S-benzylmercapturic acid (IC50 = 0.018 mu mol/L) and weaker recognition for seven other mercapturic acids (IC50 = 0.021-10 mu mol/L). Strong positive assay responses were detected in 12 urine samples obtained from persons with no known occupational exposure to exogenous electrophilic xenobiotics. Solid phase extraction and cross-reactivity indicated that the presumptive immunoreactive materials were similar in size and polarity to S-benzylmercapturic acid. The assay was more selective to mercapturic acids than the spectrophotometric thioether assay.
• An improved method for cysteine alkylation
  作者：David A. Perrey、Fatih M. Uckun

  DOI：10.1016/s0040-4039(01)00098-3

  日期：2001.3

  An improved method for the synthesis of S-alkylated cysteine derivatives with branched alkyl chains is reported. These compounds can be obtained in good yield and high purity by refluxing the cysteine thiol with the appropriate alkyl bromide in a solution of sodium ethoxide in ethanol. (C) 2001 Elsevier Science Ltd. All rights reserved.