Arg-Pro-pNA | 60189-46-0

• 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: Arg-Pro-pNA
• 英文别名: L-arginyl-L-proline p-nitroanilide；(S)-1-((S)-2-Amino-5-guanidinopentanoyl)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide；(2S)-1-[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]-N-(4-nitrophenyl)pyrrolidine-2-carboxamide
• CAS: 60189-46-0
• 化学式: C₁₇H₂₅N₇O₄
• 分子量: 391.43
• InChiKey: IUMFVSMNETWFNX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Arg-Pro-pNA 反应 0.17h， 生成 Arginylproline 、 4-硝基苯胺
  参考文献：
  名称：

  Catalytic Properties of X-Prolyl Dipeptidyl Aminopeptidase fromLactococcus lactissubsp.cremorisnTR

  摘要：

  在Lactococcus lactis subsp. cremoris nTR的内细胞膜组分上，鉴定出一种松散结合的X-脯氨酰二肽二肽基氨肽酶（X-PDAP；EC 3.4.14.5）。在细菌的后期对数生长阶段之前，X-PDAP的生物合成不断增加。X-PDAP可以水解Gly-Pro-pNA和Ala-Ala-pNA，前者的kcat/Km值约为后者的10倍。X-Pro和Pro-X的Ki比X-Ala更特异于X-PDAP。鉴定出一种以β-酪啡肽为模型的催化模式连续切割二肽的酶，并进一步表征了该酶的一些性质。

  DOI：

  10.1271/bbb.56.704
• 作为产物：
  描述：

  L-脯氨酰对硝基苯胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 Arg-Pro-pNA
  参考文献：
  名称：

  Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors

  摘要：

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.071

文献信息

• Catalytic Properties of X-Prolyl Dipeptidyl Aminopeptidase from<i>Lactococcus lactis</i>subsp.<i>cremoris</i>nTR
  作者：Tsong-Rong Yan、Shih-Ching Ho、Chia-Lung Hou

  DOI：10.1271/bbb.56.704

  日期：1992.1

  An X-prolyl dipeptidyl aminopeptidase (X-PDAP; EC 3.4.14.5) was identified to be loosely bound on the inner cell membrane fraction of Lactococcus lactis subsp. cremoris nTR. The biosynthesis of X-PDAP was continuously increased before the late-log growth phase of the bacteria. Both Gly-Pro-pNA and Ala-Ala-pNA were hydrolyzed by X-PDAP; the kcat/Km value of the former was about 10-fold that of the latter. The Ki of X-Pro and Pro-X were more specific to X-PDAP than those of X-Ala. The enzyme splitting a dipeptide sequentially from β-casomorphin as a model catalytic pattern was identified and some properties of the enzyme were further characterized.

  在Lactococcus lactis subsp. cremoris nTR的内细胞膜组分上，鉴定出一种松散结合的X-脯氨酰二肽二肽基氨肽酶（X-PDAP；EC 3.4.14.5）。在细菌的后期对数生长阶段之前，X-PDAP的生物合成不断增加。X-PDAP可以水解Gly-Pro-pNA和Ala-Ala-pNA，前者的kcat/Km值约为后者的10倍。X-Pro和Pro-X的Ki比X-Ala更特异于X-PDAP。鉴定出一种以β-酪啡肽为模型的催化模式连续切割二肽的酶，并进一步表征了该酶的一些性质。
• Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors
  作者：Guo-Chun Zhou、Zhibing Weng、Xiaoxia Shao、Fang Liu、Xin Nie、Jinsong Liu、Decai Wang、Chunguang Wang、Kai Guo

  DOI：10.1016/j.bmcl.2013.10.071

  日期：2013.12

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.