(2S)-2-[[(2S)-2-[4-[[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]methyl]triazol-1-yl]-3-phenylpropanoyl]amino]-4-methylpentanoic acid | 1454659-75-6

• 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: (2S)-2-[[(2S)-2-[4-[[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]methyl]triazol-1-yl]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
• CAS: 1454659-75-6
• 化学式: C₂₉H₃₇N₇O₆
• 分子量: 579.656
• InChiKey: OFKQNSPPTICVGO-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Fmoc-甘氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-O-叔丁基-L-酪氨酸 在 吡啶 、 2,6-二氯苯甲醛 、 苯甲酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到(2S)-2-[[(2S)-2-[4-[[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]methyl]triazol-1-yl]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
  参考文献：
  名称：

  Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity

  摘要：

  Using Cu(I)-catalyzed azide-alkyne cycloaddition in a mixed classical organic phase and solid phase peptide synthesis approach, we synthesized four analogs of Leu-enkephalin to systematically replace amides by 1,4-disubstituted[1,2,3] triazoles. The peptidomimetics obtained were characterized by competitive binding, contractility assays and ERK1/2 phosphorylation. The present study reveals that the analog bearing a triazole between Phe and Leu retains some potency, more than all the others, suggesting that the hydrogen bond acceptor capacity of the last amide of Leu-enkephalin is essential for the biological activity of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.020

文献信息

• Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity
  作者：Arnaud Proteau-Gagné、Kristina Rochon、Mélissa Roy、Pierre-Julien Albert、Brigitte Guérin、Louis Gendron、Yves L. Dory

  DOI：10.1016/j.bmcl.2013.08.020

  日期：2013.10

  Using Cu(I)-catalyzed azide-alkyne cycloaddition in a mixed classical organic phase and solid phase peptide synthesis approach, we synthesized four analogs of Leu-enkephalin to systematically replace amides by 1,4-disubstituted[1,2,3] triazoles. The peptidomimetics obtained were characterized by competitive binding, contractility assays and ERK1/2 phosphorylation. The present study reveals that the analog bearing a triazole between Phe and Leu retains some potency, more than all the others, suggesting that the hydrogen bond acceptor capacity of the last amide of Leu-enkephalin is essential for the biological activity of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.