MeO-Suc-Ala-Ala-Pro-OH | 72252-95-0

• 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: MeO-Suc-Ala-Ala-Pro-OH
• 英文别名: (3-methoxycarbonyl-1-oxopropyl)-L-alanyl-L-alanyl-L-proline；N-(4-Methoxy-4-oxobutanoyl)-L-alanyl-L-alanyl-L-proline；(2S)-1-[(2S)-2-[[(2S)-2-[(4-methoxy-4-oxobutanoyl)amino]propanoyl]amino]propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 72252-95-0
• 化学式: C₁₆H₂₅N₃O₇
• 分子量: 371.39
• InChiKey: SORPHGTXBKXLSU-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  MeO-Suc-Ala-Ala-Pro-OH 在 N-甲基吗啉 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 4.0h， 生成 N-(4-methoxy-1,4-dioxobutyl)-L-alanyl-L-alanyl-N-<2-hydroxy-3-methoxy-3-oxo-1-(phenylmethyl)propyl>-L-prolinamide
  参考文献：
  名称：

  Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G

  摘要：

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.

  DOI：

  10.1021/jm00163a063

文献信息

• Difluoromethyleneketone retroamide, a versatile concept of inactivation of proteolytic enzymes
  作者：D. Schirlin、S. Baltzer、J.M. Altenburger、C. Tarnus、J.M. Remy

  DOI：10.1016/0040-4020(95)00896-g

  日期：1996.1

  The synthesis of difluoromethyleneketone retroamides is described. Several examples of application to aspartyl or seryl proteases illustrate the versatility of this inactivation concept.
• PEET, NORTON P.;BURKHART, JOSEPH P.;ANGELASTRO, MICHAEL R.;GIROUX, EUGENE+, J. MED. CHEM., 33,(1990) N, C. 394-407
  作者：PEET, NORTON P.、BURKHART, JOSEPH P.、ANGELASTRO, MICHAEL R.、GIROUX, EUGENE+

  DOI：——

  日期：——
• OLEKSYSZYN, JOZEF;POWERS, JAMES C., BIOCHEMISTRY, 30,(1991) N, C. 485-493
  作者：OLEKSYSZYN, JOZEF、POWERS, JAMES C.

  DOI：——

  日期：——
• BACHOVCHIN, WILLIAM W.;PLAUT, ANDREW G.;KETTNER, CHARLES A.
  作者：BACHOVCHIN, WILLIAM W.、PLAUT, ANDREW G.、KETTNER, CHARLES A.

  DOI：——

  日期：——
• Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G
  作者：Norton P. Peet、Joseph P. Burkhart、Michael R. Angelastro、Eugene L. Giroux、Shujaath Mehdi、Philippe Bey、Michael Kolb、Bernhard Neises、Daniel Schirlin

  DOI：10.1021/jm00163a063

  日期：1990.1

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.