S-叔丁基-L-半胱氨酸盐酸盐 | 2481-09-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 半胱氨酸类衍生物
• 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
• 中文名称: S-叔丁基-L-半胱氨酸盐酸盐
• 中文别名: (R)-2-氨基-3-(叔丁硫基)丙酸；L-半胱氨酸叔丁酯盐酸盐；S-叔-丁基-L-半胱氨酸盐酸盐
• 英文名称: S-t-butyl-L-cysteine hydrochloride
• 英文别名: S-tert-Butyl-N-acetyl-L-cysteine hydrochloride；S-tert-Butyl-L-cysteine Hydrochloride；H-Cys(t-Bu)-OH hydrochloride；(2R)-2-amino-3-tert-butylsulfanylpropanoic acid;hydron;chloride
• CAS: 2481-09-6
• 化学式: C₇H₁₅NO₂S*ClH
• 分子量: 213.729
• InChiKey: MHBMYFJKEBCMDR-JEDNCBNOSA-N

物化性质

• 熔点：
  203-204 °C
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -2.78
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

制备方法与用途

S-叔丁基-L-半胱氨酸盐酸盐是一种半胱氨酸的衍生物。

反应信息

• 作为反应物：
  描述：

  S-叔丁基-L-半胱氨酸盐酸盐 在 氯化亚砜 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 42.1h， 生成 Boc-L-Cys(t-Bu)-OMe
  参考文献：
  名称：

  A Convenient Method for Regeneration of Free Thiol from a tert-Butyl Thioether

  摘要：

  当二甲基甲硫磺酰三氟化物（DMTST）添加到叔丁基保护的硫醇（RSt-Bu）时，会形成不对称的二硫化物RSSMe。此时，可以通过添加三甲基膦和水来获得游离硫醇（RSH）。大多数副产品都是易于去除的小有机分子。

  DOI：

  10.1055/s-2007-991091
• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 叔丁醇 以 盐酸 为溶剂， 反应 12.0h， 以90%的产率得到S-叔丁基-L-半胱氨酸盐酸盐
  参考文献：
  名称：

  tert-Butyl group as thiol protection in peptide synthesis

  摘要：

  DOI：

  10.1021/jo00322a024

文献信息

• Bioactive peptides
  申请人：ALPHARMA AS

  公开号：US20030022821A1

  公开（公告）日：2003-01-30

  The present invention provides a modified lactoferrin peptide which is cytotoxic, 7 to 25 amino acids in length, with three or more cationic residues and which has one or more extra bulky and lipophilic amino acids as compared to the native lactoferrin sequence, as well as esters, amides, salts and cyclic derivatives thereof as well as methods of preparing such peptides, pharmaceutical compositions containing such peptides and use of the peptides as medicaments, particularly as antibacterials or anti-tumoural agents.

  本发明提供一种改性乳铁蛋白肽，其具有细胞毒性，长度为7至25个氨基酸，含有三个或更多阳离子残基，并且与天然乳铁蛋白序列相比，具有一个或多个额外的笨重和亲脂氨基酸，以及其酯、酰胺、盐和环状衍生物，以及制备这些肽的方法、含有这些肽的药物组合物和将这些肽用作药物的用途，特别是作为抗菌或抗肿瘤剂。
• Chimiak,A., Roczniki Chemii, 1964, vol. 38, p. 883 - 885
  作者：Chimiak,A.

  DOI：——

  日期：——
• Acylase I-Catalyzed Deacetylation of <i>N</i>-Acetyl-<scp>l</scp>-cysteine and <i>S</i>-Alkyl-<i>N</i>-acetyl-<scp>l</scp>-cysteines
  作者：Vinita Uttamsingh、D. A. Keller、M. W. Anders

  DOI：10.1021/tx980018b

  日期：1998.7.1

  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.
• Atherton, Eric; Pinori, Masimo; Sheppard, Robert C., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2057 - 2064
  作者：Atherton, Eric、Pinori, Masimo、Sheppard, Robert C.

  DOI：——

  日期：——
• Pastuszak,J.J.; Chimiak,A., Roczniki Chemii, 1977, vol. 51, p. 1567 - 1569
  作者：Pastuszak,J.J.、Chimiak,A.

  DOI：——

  日期：——