Boc-Phe-Phe-Phe-NHOH | 143674-12-8

• 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: Boc-Phe-Phe-Phe-NHOH
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S)-1-(hydroxyamino)-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 143674-12-8
• 化学式: C₃₂H₃₈N₄O₆
• 分子量: 574.677
• InChiKey: XWVHTAXMHZPOKV-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Boc-Phe-Phe-Phe-OMe 在 盐酸羟胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以63%的产率得到Boc-Phe-Phe-Phe-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