TFA·Tyr-Pro-Phe-(N-Me)Phe-NH(CH₂)₂OH | 1471520-19-0

• 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: TFA·Tyr-Pro-Phe-(N-Me)Phe-NH(CH₂)₂OH
• 英文别名: H-Tyr-Pro-Phe-N(Me)Phe-Gly-ol.TFA；(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl]-methylamino]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid
• CAS: 1471520-19-0
• 化学式: C₂HF₃O₂*C₃₅H₄₃N₅O₆
• 分子量: 743.78
• InChiKey: FMXINHXJJBNTPF-IUQRHOJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  203
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-甲基-L-苯丙氨酸盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 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 12.51h， 生成 TFA·Tyr-Pro-Phe-(N-Me)Phe-NH(CH₂)₂OH
  参考文献：
  名称：

  Hybrid peptides endomorphin-2/DAMGO: Design, synthesis and biological evaluation

  摘要：

  Endomorphin-2 [Tyr-Pro-Phe-Phe-NH2] and DAMGO [Tyr-D-Ala-Gly-(N-Me)Phe-Gly-ol] are natural (EM2) and synthetic (DAMGO) opioid peptides both selective for mu opioid receptor with high analgesic activity. In this work we report synthesis, in vitro and in vivo biological evaluation of five new hybrid EM2/DAMGO analogues, with the aim to obtain compounds with high affinity at mu-opioid receptor, high activity in animal nociception tests (hot plate and tail flick) and improved enzymatic stability. Double N-methylation on both Phe residues and C-terminal ethanolamide led to analogue 6e, which possesses a good in vitro mu affinity (K-i(mu) = 34 nM), combined with a remarkable in vivo antinociceptive activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.044

文献信息

• Hybrid peptides endomorphin-2/DAMGO: Design, synthesis and biological evaluation
  作者：Adriano Mollica、Roberto Costante、Azzurra Stefanucci、Francesco Pinnen、Grazia Luisi、Stefano Pieretti、Anna Borsodi、Engin Bojnik、Sándor Benyhe

  DOI：10.1016/j.ejmech.2013.07.044

  日期：2013.10

  Endomorphin-2 [Tyr-Pro-Phe-Phe-NH2] and DAMGO [Tyr-D-Ala-Gly-(N-Me)Phe-Gly-ol] are natural (EM2) and synthetic (DAMGO) opioid peptides both selective for mu opioid receptor with high analgesic activity. In this work we report synthesis, in vitro and in vivo biological evaluation of five new hybrid EM2/DAMGO analogues, with the aim to obtain compounds with high affinity at mu-opioid receptor, high activity in animal nociception tests (hot plate and tail flick) and improved enzymatic stability. Double N-methylation on both Phe residues and C-terminal ethanolamide led to analogue 6e, which possesses a good in vitro mu affinity (K-i(mu) = 34 nM), combined with a remarkable in vivo antinociceptive activity. (C) 2013 Elsevier Masson SAS. All rights reserved.