N-acetyl-S-[N-(methyl)thiocarbamoyl]-L-cysteine | 31655-50-2

• 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-acetyl-S-[N-(methyl)thiocarbamoyl]-L-cysteine
• 英文别名: (N-acetyl-S-methylthiocarbamoyl)cysteine；N-α-Acetyl-S-methylthiocarbamoyl-L-cystein；Cysteine, N-acetyl-, methyldithiocarbamate (ester), L-；(2R)-2-acetamido-3-(methylcarbamothioylsulfanyl)propanoic acid
• CAS: 31655-50-2
• 化学式: C₇H₁₂N₂O₃S₂
• 分子量: 236.316
• InChiKey: XUTOTHUXOQJOJN-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 异硫氰酸甲酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N-acetyl-S-[N-(methyl)thiocarbamoyl]-L-cysteine
  参考文献：
  名称：

  Characterization of Protein Adducts Produced by N-Methyldithiocarbamate and N-Methyldithiocarbamate Esters

  摘要：

  The toxicity of N-methyldithiocarbamate may be mediated through decomposition to more biologically active compounds. Two principal products, CS2 and methyl isothiocyanate, have the potential to interact covalently with macromolecules in biological systems. In this investigation the ability of N-methyldithiocarbamate to generate methyl isothiocyanate and CS2 under physiological conditions resulting in acylation and covalent cross-linking of proteins was examined using C-13 NMR and GC/MS. Two N-methyldithiocarbamate esters, S-methyl N-methyldithiocarbamate and (N-acetyl-S-methylthiocarbamoyl)cysteine were also investigated to evaluate the acylating ability of sulfhydryl conjugates of N-methyldithiocarbamate. The predominant and most stable adduct produced by the free dithiocarbamate and its S-substituted esters was methylthiourea on epsilon-lysyl and N-terminal alpha-amino groups. Derivatization on N-terminal amino groups progressed more rapidly for the dithiocarbamate than for its mercapturate. Methylurea protein adducts were also produced by the dithiocarbamate and its esters, suggesting production of methyl isocyanate in the decomposition of N-methyldithiocarbamate. Covalent cross-linking of beta-lactoglobulin by N-methyldithiocarbamate resulting from its decomposition to CS2 was observed using denaturing polyacrylamide gel electrophoresis. These results demonstrate the ability of a monoalkyldithiocarbamate to acylate protein amino groups and effect covalent cross-linking. These processes represent molecular mechanisms that may contribute to the toxicity of this class of compounds.

  DOI：

  10.1021/tx00044a011

文献信息

• Synthesis of isothiocyanate-derived mercapturic acids
  作者：Martijn Vermeulen、Binne Zwanenburg、Gordon J.F Chittenden、Hans Verhagen

  DOI：10.1016/s0223-5234(03)00141-7

  日期：2003.7

  Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.