tert-butyl (2S)-1-[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-(phenylmethoxycarbonylamino)butyl]amino]hexanoyl]pyrrolidine-2-carboxylate | 194484-81-6

• 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: tert-butyl (2S)-1-[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-(phenylmethoxycarbonylamino)butyl]amino]hexanoyl]pyrrolidine-2-carboxylate
• CAS: 194484-81-6
• 化学式: C₃₆H₅₈N₄O₉
• 分子量: 690.878
• InChiKey: GHANNYQBBOLXRZ-KCHLEUMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-1-[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-(phenylmethoxycarbonylamino)butyl]amino]hexanoyl]pyrrolidine-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以100%的产率得到tert-butyl (2S)-1-[(2S)-2-[[(2S)-2-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutyl]amino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]pyrrolidine-2-carboxylate
  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
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -15.0~25.0 ℃ 、101.33 kPa 条件下， 反应 13.08h， 生成 tert-butyl (2S)-1-[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-(phenylmethoxycarbonylamino)butyl]amino]hexanoyl]pyrrolidine-2-carboxylate
  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

• 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.