(S)-2-{[Benzyloxycarbonyl-((S)-1-isopropylcarbamoyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester | 189823-26-5

• 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: (S)-2-{[Benzyloxycarbonyl-((S)-1-isopropylcarbamoyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 189823-26-5
• 化学式: C₂₄H₃₇N₃O₅
• 分子量: 447.575
• InChiKey: SHSYBEKFCHRZJP-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.18
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{[Benzyloxycarbonyl-((S)-1-isopropylcarbamoyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 在 N-甲基吗啉 、 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 [(S)-1-(2,2-Dimethyl-propionyl)-pyrrolidin-2-ylmethyl]-((S)-1-isopropylcarbamoyl-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Structural Comparison of Homologous Reduced Peptide, Reduced Azapeptide, Iminoazapeptide, and Methyleneoxypeptide Analogues

  摘要：

  The homologous RCO-Pro-Xaa-NHR' model pseudodipeptides containing the reduced peptide ((CCH2NHCalpha)-C-alpha), reduced azapeptide ((CCH2NHNalpha)-C-alpha), methyleneoxy ((CCH2OCalpha)-C-alpha), and iminoazapeptide ((CCH)-C-alpha=NNalpha) surrogate of the middle amide group have been prepared. Their structural analysis has been carried out in solution by H-1 NMR and IR spectroscopy and in the solid state by X-ray diffraction. The last three fragments, not protonated in the pH range 2-12, and the reduced fragment in its neutral amine form induce quite similar molecular structures characterized by a hydrogen bond between NHR' and the N/O atom replacing the amide NH group and closing a five-membered cycle. The neutral amine or protonated ammonium state of the reduced amide fragment, with a pK(a) value of about 7, depends on the environment. Protonation induces a conformational transition due to the strong proton donating properties of the ammonium group which interacts with the RCO carbonyl.

  DOI：

  10.1021/ja980937o
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 N-甲基吗啉 、 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 丙酮 为溶剂， 生成 (S)-2-{[Benzyloxycarbonyl-((S)-1-isopropylcarbamoyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Structural Comparison of Homologous Reduced Peptide, Reduced Azapeptide, Iminoazapeptide, and Methyleneoxypeptide Analogues

  摘要：

  The homologous RCO-Pro-Xaa-NHR' model pseudodipeptides containing the reduced peptide ((CCH2NHCalpha)-C-alpha), reduced azapeptide ((CCH2NHNalpha)-C-alpha), methyleneoxy ((CCH2OCalpha)-C-alpha), and iminoazapeptide ((CCH)-C-alpha=NNalpha) surrogate of the middle amide group have been prepared. Their structural analysis has been carried out in solution by H-1 NMR and IR spectroscopy and in the solid state by X-ray diffraction. The last three fragments, not protonated in the pH range 2-12, and the reduced fragment in its neutral amine form induce quite similar molecular structures characterized by a hydrogen bond between NHR' and the N/O atom replacing the amide NH group and closing a five-membered cycle. The neutral amine or protonated ammonium state of the reduced amide fragment, with a pK(a) value of about 7, depends on the environment. Protonation induces a conformational transition due to the strong proton donating properties of the ammonium group which interacts with the RCO carbonyl.

  DOI：

  10.1021/ja980937o

文献信息

• The non protonable reduced aza-peptide fragment
  作者：Régis Vanderesse、Laurent David、Vincent Grand、Michel Marraud、Jean Paul Mangeot、André Aubry

  DOI：10.1016/s0040-4039(97)00410-3

  日期：1997.4

  The reduced aza-peptide fragment (C-alpha-CH2-NH-N(alpha)R-CO-NH-C-alpha) is obtained by reduction of the semicarbazone moiety (C-alpha-CH=N-N(alpha)R-CO-NH-C-alpha) in an imino aza-peptide. It differs from the aminomethylene link (C-alpha-CH2-NH-C(alpha)HR-CO-NH-C-alpha) found in the reduced peptides by the absence of protonation in water in the 2-12 pH range. The reduced aza-analogue of the Pro-Ala dipeptide has been studied in solution by H-1-NMR and IR spectroscopy, and in the solid state by X-ray diffraction. Its structure is quite similar to that of the neutral reduced dipeptide analogue in solution. (C) 1997 Elsevier Science Ltd.