(2R)-2-acetamido-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-5-(diaminomethylideneamino)pentanamide | 1402723-42-5

• 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: (2R)-2-acetamido-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-5-(diaminomethylideneamino)pentanamide
• CAS: 1402723-42-5
• 化学式: C₁₇H₂₆N₆O₃
• 分子量: 362.432
• InChiKey: LVUYIEJZQHIBNE-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙酰基-D-精氨酸二水合物 、 L-苯丙氨酰胺 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 (2R)-2-acetamido-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-5-(diaminomethylideneamino)pentanamide
  参考文献：
  名称：

  Opioid Activity Profiles of Oversimplified Peptides Lacking in the Protonable N-Terminus

  摘要：

  Recently, we described cyclopeptide opioid agonists containing the D-Trp-Phe sequence. To expand the scope of this atypical pharmacophore, we tested the activity profiles of the linear peptides Ac-Xaa-Phe-Yaa (Xaa = L/D-Trp, D-His/Lys/Arg; Yaa = H, GlyNH(2)). Ac-D-Trp-PheNH(2) appeared to be the minimal binding sequence, while Ac-D-Trp-Phe-GlyNH(2) emerged, as the first noncationizable short peptide (partial) agonist with high mu-opioid receptor affinity and selectivity. Conformational analysis suggested that 5 adopts in solution a beta-turn conformation.

  DOI：

  10.1021/jm301213s

文献信息

• Opioid Activity Profiles of Oversimplified Peptides Lacking in the Protonable N-Terminus
  作者：Rossella De Marco、Alessandra Tolomelli、Santi Spampinato、Andrea Bedini、Luca Gentilucci

  DOI：10.1021/jm301213s

  日期：2012.11.26

  Recently, we described cyclopeptide opioid agonists containing the D-Trp-Phe sequence. To expand the scope of this atypical pharmacophore, we tested the activity profiles of the linear peptides Ac-Xaa-Phe-Yaa (Xaa = L/D-Trp, D-His/Lys/Arg; Yaa = H, GlyNH(2)). Ac-D-Trp-PheNH(2) appeared to be the minimal binding sequence, while Ac-D-Trp-Phe-GlyNH(2) emerged, as the first noncationizable short peptide (partial) agonist with high mu-opioid receptor affinity and selectivity. Conformational analysis suggested that 5 adopts in solution a beta-turn conformation.