Tyr-Pro-Phe-Phe-NH2 | 579490-96-3

• 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: Tyr-Pro-Phe-Phe-NH2
• 英文别名: H-Pro-Phe-Phe-NH2；endomorphin-2；YPFF-NH2；(2S)-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide
• CAS: 579490-96-3
• 化学式: C₂₃H₂₈N₄O₃
• 分子量: 408.5
• InChiKey: GQTQFZUTXSDLLQ-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tyr-Pro-Phe-Phe-NH2 在 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 D,L-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylamide-Pro-Phe-Phe-NH2
  参考文献：
  名称：

  6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides

  摘要：

  6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (6Htc) has been proposed as a rigid mimic of tyrosine conformation in opioid ligand-receptor complex. The significant receptor binding to mu and delta opioid receptors of respective analogues of deltorphin, dermorphin, and endomorphin with D,L-6Htc prove initial prediction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.075
• 作为产物：
  描述：

  L-苯丙氨酰胺 在 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 Tyr-Pro-Phe-Phe-NH2
  参考文献：
  名称：

  6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides

  摘要：

  6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (6Htc) has been proposed as a rigid mimic of tyrosine conformation in opioid ligand-receptor complex. The significant receptor binding to mu and delta opioid receptors of respective analogues of deltorphin, dermorphin, and endomorphin with D,L-6Htc prove initial prediction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.075

文献信息

• Discovery of Dipeptides with High Affinity to the Specific Binding Site for Substance P₁₋₇
  作者：Rebecca Fransson、Milad Botros、Christian Sköld、Fred Nyberg、Gunnar Lindeberg、Mathias Hallberg、Anja Sandström

  DOI：10.1021/jm901352b

  日期：2010.3.25

  Substance P 1-7 (SP1-7, H-Arg-Pro-Lys-Pro-Gln-Gln-Phe-OH) is the major bioactive metabolite of substance P. The interest in this heptapeptide originates from the observation that it modulates, and in certain cases opposes the effects of the parent peptide. e.g., the nociceptive effect. The p-opioid receptor agonist endomorphin-2 (EM-2, H-Tyr-Pro-Phe-Phe-NH2) has been found to also interact with the specific binding site of SP1-7 with only a 10-fold lower affinity compared to the native peptide. Considering the smaller size of EM-2 compared to the target heptapeptide, it was selected as a lead compound in the development of low-molecular-weight ligands to the SP1-7 binding site. An alanine scan and truncation study led to the unexpected discovery of the dipeptide H-Phe-Phe-NH2 (K-i = 1.5 nM), having equal affinity as the endogenous heptapeptide SP1-7. Moreover, the studies show that the C-terminal phenylalanine amide is crucial for the affinity of the dipeptide.
• 6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides
  作者：Emanuela Sperlinga、Piotr Kosson、Zofia Urbanczyk-Lipkowska、Giuseppe Ronsisvalle、Daniel B. Carr、Andrzej W. Lipkowski

  DOI：10.1016/j.bmcl.2005.03.075

  日期：2005.5

  6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (6Htc) has been proposed as a rigid mimic of tyrosine conformation in opioid ligand-receptor complex. The significant receptor binding to mu and delta opioid receptors of respective analogues of deltorphin, dermorphin, and endomorphin with D,L-6Htc prove initial prediction. (c) 2005 Elsevier Ltd. All rights reserved.