(2S)-2-[4-[[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]triazol-1-yl]-3-phenylpropanoic acid | 1454659-69-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-2-[4-[[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]triazol-1-yl]-3-phenylpropanoic acid
• CAS: 1454659-69-8
• 化学式: C₂₂H₃₀N₄O₆
• 分子量: 446.503
• InChiKey: AFKTUSZJFZWJET-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 (2S)-2-[4-[[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]triazol-1-yl]-3-phenylpropanoic acid 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以83%的产率得到N-Fmoc-(4-(aminomethyl)-triazol-1-yl)acetic 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
• 作为产物：
  描述：

  L-苯丙氨酸 在 triflic azide 、 2,6-二甲基吡啶 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 32.0h， 生成 (2S)-2-[4-[[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]triazol-1-yl]-3-phenylpropanoic 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.