Boc-Met-β-Ala-Phe-OMe | 672912-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Boc-Met-β-Ala-Phe-OMe
• 英文别名: Boc-Met-beta-Ala-Phe-OMe；methyl (2S)-2-[3-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoyl]amino]propanoylamino]-3-phenylpropanoate
• CAS: 672912-17-3
• 化学式: C₂₃H₃₅N₃O₆S
• 分子量: 481.613
• InChiKey: ZNUDFJWVDJSQLY-ROUUACIJSA-N

物化性质

• 沸点：
  721.7±60.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲酸 、 Boc-Met-β-Ala-Phe-OMe 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以93%的产率得到HCO-Met-β-Ala-Phe-OMe
  参考文献：
  名称：

  Synthesis and activity of HCO–Met–Leu–Phe–OMe analogues containing β-alanine or taurine at the central position

  摘要：

  New synthetic analogues of the chemotactic N-formyltripeptide HCO-Met-Leu-Phe-OMe have been synthesized. The reported new models, namely Boc-Met-beta-Ala-Phe-OMe (1), HCO-Met-beta-Ala-Phe-OMe (2), Boc-Met-Tau-Phe-OMe (3), HCO-Met-Tau-Phe-OMe (4) and HCl.Met-Tau-Phe-OMe (5), are characterized by the presence at the central position of a residue of beta-alanine or 2-aminoethanesulfonic acid (taurine) replacing the native L-leucine. Whereas tripeptides 1 and 2 have been found quite inactive as chemoattractants, all the three models containing the Tau residue exhibit a remarkable activity. Superoxide anion production and lysozyme release have been also evaluated and the biological results are discussed together with the conformational preferences of the examined models.

  DOI：

  10.1016/s0014-827x(03)00165-4
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Boc-Met-β-Ala-Phe-OMe
  参考文献：
  名称：

  Synthesis and activity of HCO–Met–Leu–Phe–OMe analogues containing β-alanine or taurine at the central position

  摘要：

  New synthetic analogues of the chemotactic N-formyltripeptide HCO-Met-Leu-Phe-OMe have been synthesized. The reported new models, namely Boc-Met-beta-Ala-Phe-OMe (1), HCO-Met-beta-Ala-Phe-OMe (2), Boc-Met-Tau-Phe-OMe (3), HCO-Met-Tau-Phe-OMe (4) and HCl.Met-Tau-Phe-OMe (5), are characterized by the presence at the central position of a residue of beta-alanine or 2-aminoethanesulfonic acid (taurine) replacing the native L-leucine. Whereas tripeptides 1 and 2 have been found quite inactive as chemoattractants, all the three models containing the Tau residue exhibit a remarkable activity. Superoxide anion production and lysozyme release have been also evaluated and the biological results are discussed together with the conformational preferences of the examined models.

  DOI：

  10.1016/s0014-827x(03)00165-4