N-(N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester | 90826-23-6

• 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: N-(N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester
• 英文别名: Cbz-Lys(Boc)-Pro-OBn；benzyl (2S)-1-[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoyl]pyrrolidine-2-carboxylate
• CAS: 90826-23-6
• 化学式: C₃₁H₄₁N₃O₇
• 分子量: 567.682
• InChiKey: RJVMPJQARBNJFO-UIOOFZCWSA-N

物化性质

• 沸点：
  742.9±60.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester 在 palladium on activated charcoal sodium hydroxide 、 Dowex 50 (H⁺, 50-100 mesh) 、 氢气 、 sodium cyanoborohydride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 15.0h， 生成 赖诺普利
  参考文献：
  名称：

  N2-[（S）-1-羧基-3-苯基丙基] -L-赖氨酰-L-脯氨酸（Lisinopril）的合成

  摘要：

  描述了N2-[（S）-1-羧基-3-苯基丙基] -L-赖氨酰-L-脯氨酸（赖诺普利，MK-521）的合成和某些光谱性质。该化合物抑制血管紧张素转化酶，IC50为1.2 X 10（-9）M。

  DOI：

  10.1002/jps.2600740330
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 N-(N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester
  参考文献：
  名称：

  NAcSDKP Analogues Resistant to Angiotensin-Converting Enzyme

  摘要：

  Two series of analogues of the tetrapeptide NAcSDKP, an inhibitor of hematopoietic stem cell proliferation, were prepared, and their enzymatic stability toward rabbit lung angiotensin-converting enzyme (ACE) was evaluated as well as their capacity to inhibit NAcSDKP hydrolysis by this enzyme. In the first series, each of the peptide bonds has been successively replaced by an aminomethylene bond. In the second one, the C-terminus of the peptide has been modified by decarboxylation or amidation. The results reported here indicate that all of these molecules but one have good stability toward the enzyme but none of the compounds is able to inhibit NAcSDKP hydrolysis by ACE.

  DOI：

  10.1021/jm9701132

文献信息

• Synthesis of N2-[(S)-1-Carboxy-3-phenylpropyl]-L-lysyl-L-proline (Lisinopril)
  作者：M.T. Wu、A.W. Douglas、D.L. Ondeyka、L.G. Payne、T.J. Ikeler、H. Joshua、A.A. Patchett

  DOI：10.1002/jps.2600740330

  日期：1985.3

  The synthesis and some of the spectral properties of N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline (lisinopril, MK-521) are described. This compound inhibits angiotensin-converting enzyme with an IC50 of 1.2 X 10(-9) M.

  描述了N2-[（S）-1-羧基-3-苯基丙基] -L-赖氨酰-L-脯氨酸（赖诺普利，MK-521）的合成和某些光谱性质。该化合物抑制血管紧张素转化酶，IC50为1.2 X 10（-9）M。
• NAcSDKP Analogues Resistant to Angiotensin-Converting Enzyme
  作者：Sandrine Gaudron、Marie-Thérèse Adeline、Pierre Potier、Josiane Thierry

  DOI：10.1021/jm9701132

  日期：1997.11.1

  Two series of analogues of the tetrapeptide NAcSDKP, an inhibitor of hematopoietic stem cell proliferation, were prepared, and their enzymatic stability toward rabbit lung angiotensin-converting enzyme (ACE) was evaluated as well as their capacity to inhibit NAcSDKP hydrolysis by this enzyme. In the first series, each of the peptide bonds has been successively replaced by an aminomethylene bond. In the second one, the C-terminus of the peptide has been modified by decarboxylation or amidation. The results reported here indicate that all of these molecules but one have good stability toward the enzyme but none of the compounds is able to inhibit NAcSDKP hydrolysis by ACE.