S-(3,4-二甲基苄基)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-半胱氨酸 | 41117-66-2

• 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
• 中文名称: S-(3,4-二甲基苄基)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-半胱氨酸
• 英文名称: N-Boc-S-<(3,4-dimethylphenyl)methyl>-L-cysteine
• 英文别名: N-tert-butoxycarbonyl-S-(3,4-dimethylbenzyl)-L-cysteine；N^α-Boc-(S-3,4-Me2Bzl)-Cys；Boc-Cys(Bzl(Me)2)-OH；N^α-Boc-S-(3,4-dimethylbenzyl)cystein；Boc-cys(3,4-dimethylbenzyl)-OH；(2R)-3-[(3,4-dimethylphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 41117-66-2
• 化学式: C₁₇H₂₅NO₄S
• 分子量: 339.456
• InChiKey: AYUOVKILVZAKFO-AWEZNQCLSA-N

物化性质

• 沸点：
  508.7±50.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  S-(3,4-二甲基苄基)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-半胱氨酸 在 N-甲基吗啉 、 氯化亚砜 、 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 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 ethyl (2R)-2-[[(2R)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]-3-[(3,4-dimethylphenyl)methylsulfanyl]propanoate
  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：

  3,4-二甲基氯苄 在 sodium hydroxide 、 氨 、 氯化铵 作用下， 以 1,4-二氧六环 为溶剂， 生成 S-(3,4-二甲基苄基)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-半胱氨酸
  参考文献：
  名称：

  人垂体生长激素。36.羧基末端环状十二肽的固相合成。

  摘要：

  DOI：

  10.1021/jo00960a026

文献信息

• ACTIVATION OF CONVENTIONAL<i>S</i>-PROTECTING GROUPS OF CYSTEINE BY CONVERSION INTO THE 3-NITRO-2-PYRIDINESULFENYL (NPYS) GROUP
  作者：Rei Matsueda、Susumu Higashida、Richard J. Ridge、Gary R. Matsueda

  DOI：10.1246/cl.1982.921

  日期：1982.6.5

  All of the conventional S-protecting groups of cysteine which were tested could be selectively converted to the 3-nitro-2-pyridinesulfenyl (Npys) group after treatment with an appropriate Npys halide. Unidirectional formation of an unsymmetrical disulfide bond is possible when Cys (Npys) is mixed with a free thiol of another Cys residue. Some of these features were exploited during the solid phase

  在用适当的 Npys 卤化物处理后，所有测试的半胱氨酸的常规 S-保护基团都可以选择性地转化为 3-硝基-2-吡啶硫基 (Npys) 基团。当 Cys (Npys) 与另一个 Cys 残基的游离硫醇混合时，可以单向形成不对称的二硫键。在赖氨酸8-加压素的固相合成过程中利用了这些特征中的一些。
• Structure-activity studies of highly potent cyclic [Cys4, Cys10]melanotropin analogs
  作者：James J. Knittel、Tomi K. Sawyer、Victor J. Hruby、Mac E. Hadley

  DOI：10.1021/jm00356a002

  日期：1983.2
• Characterization of Novel Isocyanate-Derived Metabolites of the Formamide N-Formylamphetamine with the Combined Use of Electrospray Mass Spectrometry and Stable Isotope Methodology
  作者：Anthony G. Borel、Frank S. Abbott

  DOI：10.1021/tx00048a010

  日期：1995.9

  Bioactivation of the formamide N-formylamphetamine (NFA) to 1-methyl-2-phenylethyl isocyanate (MPIC) was investigated in rats by screening bile and urine for conjugates subsequent to the phase I event. NFA was administered to rats as a mixture of protio- and pentadeuteriophenyl analogues to gain insight into the carbamoylating activity of MPIC when traced by electrospray liquid chromatography/mass spectrometry (LC/MS). An LC/MS contour generated by recording the summed mass spectrum as a function of chromatographic retention time allowed four biliary metabolites to be identified from four sets of doublets, with the peak of each doublet offset by 5 amu and ca. 0.07 min. Tandem mass spectrometry experiments allowed these metabolites to be attributed structurally to the glutathione, cysteinylglycine, cysteine, and N-acetylcysteine conjugates of the isocyanate MPIC. These assignments were subsequently validated by comparison of the LC/MS properties of the metabolites to synthetic reference compounds. Only the carbamoylated N-acetylcysteine conjugate was detected in urine. The observed excretion in bile of all metabolites of the mercapturate pathway is novel for formamide metabolism. NFA can thus be added to the short list of compounds that are eliminated in this fashion. Factors envisioned as contributory to this metabolic profile in bile include hepatorenal, enterohepatic, and biliary-hepatic cycling, in addition to possible equilibrium exchange of the isocyanate from thiocarbamate conjugates to endogenous free thiols during the course of biliary transit.
• US3933784A
  申请人：——

  公开号：US3933784A

  公开（公告）日：1976-01-20
• US4062815A
  申请人：——

  公开号：US4062815A

  公开（公告）日：1977-12-13