S-(1,1-二甲基乙基)-L-半胱氨酸甲酯盐酸盐 | 58336-84-8

• 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-(1,1-二甲基乙基)-L-半胱氨酸甲酯盐酸盐
• 英文名称: S-(1,1-dimethylethyl)-L-cysteine methyl ester hydrochloride
• 英文别名: S-tert-Butyl-L-cysteine Methyl Ester Hydrochloride；H-Cys(t-Bu)-OMe hydrochloride；Cys(t-Bu)-OMe；methyl (2R)-2-amino-3-tert-butylsulfanylpropanoate;hydrochloride
• CAS: 58336-84-8
• 化学式: C₈H₁₇NO₂S*ClH
• 分子量: 227.755
• InChiKey: GMXMUPBEPPCIDZ-RGMNGODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(1,1-二甲基乙基)-L-半胱氨酸甲酯盐酸盐 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (2R)-2-[[(2S)-2-benzyl-3-sulfanylpropanoyl]amino]-3-tert-butylsulfanylpropanoic acid
  参考文献：
  名称：

  Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S-alkylcysteine derivatives

  摘要：

  A broad series of N-(3-mercaptoacyl) amino acid derivatives was evaluated for their ability to inhibit atriopeptidase (neutral endopeptidase, EC 3.4.24.11) in vitro and in vivo. Structural parameters studied were (i) the substituent on the 2-position of the 3-mercaptopropionyl moiety, (ii) the amino acid component, (iii) the S-terminal derivative, and (iv) the C-terminal derivative. Optimum activity was observed for derivatives of methionine and S-alkylcysteines. N-[3-Mercapto-2(S)-[(2-methylphenyl)methyl]-1-oxopropyl]-L-methionine was identified as a highly effective inhibitor of atriopeptidase meriting evaluation as a potential cardiovascular therapeutic agent.

  DOI：

  10.1021/jm00041a026
• 作为产物：
  描述：

  甲醇 、 N-叔丁氧羰基-S-叔丁基-L-半胱氨酸 在 氯化亚砜 作用下， 反应 21.0h， 以75%的产率得到S-(1,1-二甲基乙基)-L-半胱氨酸甲酯盐酸盐
  参考文献：
  名称：

  Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S-alkylcysteine derivatives

  摘要：

  A broad series of N-(3-mercaptoacyl) amino acid derivatives was evaluated for their ability to inhibit atriopeptidase (neutral endopeptidase, EC 3.4.24.11) in vitro and in vivo. Structural parameters studied were (i) the substituent on the 2-position of the 3-mercaptopropionyl moiety, (ii) the amino acid component, (iii) the S-terminal derivative, and (iv) the C-terminal derivative. Optimum activity was observed for derivatives of methionine and S-alkylcysteines. N-[3-Mercapto-2(S)-[(2-methylphenyl)methyl]-1-oxopropyl]-L-methionine was identified as a highly effective inhibitor of atriopeptidase meriting evaluation as a potential cardiovascular therapeutic agent.

  DOI：

  10.1021/jm00041a026

文献信息

• A Convenient Method for Regeneration of Free Thiol from a <i>tert</i>-Butyl Thioether
  作者：Douglas Grotjahn、Elijah Kragulj、Jeffery Gustafson

  DOI：10.1055/s-2007-991091

  日期：——

  When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed.

  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。
• tert-Butyl group as thiol protection in peptide synthesis
  作者：Juliusz Jacek Pastuszak、Andrzej Chimiak

  DOI：10.1021/jo00322a024

  日期：1981.4
• US5721361A
  申请人：——

  公开号：US5721361A

  公开（公告）日：1998-02-24