pGlu-Phe-Phe-Gly-OEt | 62307-62-4

• 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: pGlu-Phe-Phe-Gly-OEt
• 英文别名: ethyl 2-[[(2S)-2-[[(2S)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]acetate
• CAS: 62307-62-4
• 化学式: C₂₇H₃₂N₄O₆
• 分子量: 508.574
• InChiKey: QORQOIAYYJJDPX-FKBYEOEOSA-N

物化性质

• 沸点：
  901.1±65.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  142.7
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  pGlu-Phe-Phe-Gly-OEt 在 sodium hydroxide 、 羟胺 作用下， 以 乙醇 为溶剂， 生成 pGlu-Phe-Phe-Gly-NHOH
  参考文献：
  名称：

  Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues

  摘要：

  A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized. Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology and these were reacted with excess hydroxylamine in either ethanol or NN-dimethylformamide. The products were characterized by chromatographic methods, amino acid analysis and fast atom bombardment mass spectrometry. The inhibition of the degradation of the radiolabelled substrate desamino-[3-I-125-tyroSyl5]SP(5-11) ([(I-125)BH5]SP(5-11)) by these compounds in rat hypothalamus preparations was determined. The most potent inhibitors found were Boc-Phe-Phe-Phe-NHOH (12d, IC50 = 4-mu-M), Boc-Phe-Phe-Trp-NHOH (9, IC50 = 5-mu-M) and desamino-Tyr-Phe-Phe-Gly-NHOH (22, IC50 = 1.8-mu-M). A model describing the interaction of these compounds with the active site is proposed.

  DOI：

  10.1016/0223-5234(92)90001-h
• 作为产物：
  描述：

  Boc-L-苯丙氨酰-苯丙氨酸 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 pGlu-Phe-Phe-Gly-OEt
  参考文献：
  名称：

  Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues

  摘要：

  A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized. Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology and these were reacted with excess hydroxylamine in either ethanol or NN-dimethylformamide. The products were characterized by chromatographic methods, amino acid analysis and fast atom bombardment mass spectrometry. The inhibition of the degradation of the radiolabelled substrate desamino-[3-I-125-tyroSyl5]SP(5-11) ([(I-125)BH5]SP(5-11)) by these compounds in rat hypothalamus preparations was determined. The most potent inhibitors found were Boc-Phe-Phe-Phe-NHOH (12d, IC50 = 4-mu-M), Boc-Phe-Phe-Trp-NHOH (9, IC50 = 5-mu-M) and desamino-Tyr-Phe-Phe-Gly-NHOH (22, IC50 = 1.8-mu-M). A model describing the interaction of these compounds with the active site is proposed.

  DOI：

  10.1016/0223-5234(92)90001-h

文献信息

• Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues
  作者：A Ewenson、R Laufer、J Frey、M Chorev、Z Selinger、C Gilon

  DOI：10.1016/0223-5234(92)90001-h

  日期：1992.4

  A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized. Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology and these were reacted with excess hydroxylamine in either ethanol or NN-dimethylformamide. The products were characterized by chromatographic methods, amino acid analysis and fast atom bombardment mass spectrometry. The inhibition of the degradation of the radiolabelled substrate desamino-[3-I-125-tyroSyl5]SP(5-11) ([(I-125)BH5]SP(5-11)) by these compounds in rat hypothalamus preparations was determined. The most potent inhibitors found were Boc-Phe-Phe-Phe-NHOH (12d, IC50 = 4-mu-M), Boc-Phe-Phe-Trp-NHOH (9, IC50 = 5-mu-M) and desamino-Tyr-Phe-Phe-Gly-NHOH (22, IC50 = 1.8-mu-M). A model describing the interaction of these compounds with the active site is proposed.