N-acetyl-S-2-methylpropyl-L-cysteine | 210910-23-9

• 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-2-methylpropyl-L-cysteine
• 英文别名: S-Isobutyl-N-acetyl-L-cysteine；(2R)-2-acetamido-3-(2-methylpropylsulfanyl)propanoic acid
• CAS: 210910-23-9
• 化学式: C₉H₁₇NO₃S
• 分子量: 219.305
• InChiKey: IKWOSEYSLSAGCM-QMMMGPOBSA-N

物化性质

• 沸点：
  433.7±40.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-S-2-methylpropyl-L-cysteine 在 pig kidney acylase I 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 生成 S-isobutyl-L-cysteine
  参考文献：
  名称：

  Acylase I-Catalyzed Deacetylation of N-Acetyl-l-cysteine and S-Alkyl-N-acetyl-l-cysteines

  摘要：

  The aminoacylase that catalyzes the hydrolysis of N-acetyl-L-cysteine (NAC) was identified as acylase I after purification by column chromatography and electrophoretic analysis. Rat kidney cytosol was fractionated by ammonium sulfate precipitation, and the proteins were separated by ion-exchange column chromatography, gel-filtration column chromatography, and hydrophobic interaction column chromatography. Acylase activity with NAC and N-acetyl-L-methionine (NAM), a known substrate for acylase I, as substrates coeluted during all chromatographic steps. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that the protein was purified to near homogeneity and had a subunit M-r of 43 000, which is identical with the M-r of acylase I from porcine kidney and bovine liver. n-Butylmalonic acid was a slow-binding inhibitor of acylase I and inhibited the deacetylation of NAC with a K-i of 192 +/- 27 mu M These results show that acylase I catalyzes the deacetylation of NAG. The acylase I-catalyzed deacetylation of a range of S-alkyl-N-acetyl-L-cysteines, their carbon and oxygen analogues, and the selenium analogue of NAM was also studied with porcine kidney acylase I. The specific activity of the acylase I-catalyzed deacetylation of these substrates was related to their calculated molar volumes and lag P values. The S-alkyl-N-acetyl-L-cysteines with short (C-0-C-3) and unbranched S-alkyl substituents were good acylase I substrates, whereas the S-alkyl-N-acetyl-L-cysteines with long (>C-3) and branched S-alkyl substituents were poor acylase I substrates. The carbon and oxygen analogues of S-methyl-N-acetyl-L-cysteine and the carbon analogue of S-ethyl-N-acetyl-L-cysteine were poor acylase I substrates, whereas the selenium analogue of NAM was a good acylase I substrate.

  DOI：

  10.1021/tx980018b
• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 溴代异丁烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以81%的产率得到N-acetyl-S-2-methylpropyl-L-cysteine
  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