TIPP | 146369-65-5

• 物质功能分类: 生物化工 - 多肽
• 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: TIPP
• 英文别名: H-Tyr-((3S)-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl)-Phe-Phe-OH；H-Tyr-Tic-Phe-Phe-OH；Tyr-Tic-Phe-Phe；Tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine；(2S)-2-[[(2S)-2-[[(3S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoic acid
• CAS: 146369-65-5
• 化学式: C₃₇H₃₈N₄O₆
• 分子量: 634.732
• InChiKey: JYOUATXRHWNDDW-YRCZKMHPSA-N

物化性质

• 沸点：
  994.2±65.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 Boc-L-酪氨酸 、 N-叔丁氧羰基-(S)-1,2,3,4-四氢异喹啉-3-羧酸 生成 TIPP
  参考文献：
  名称：

  Side Chain Methyl Substitution in the δ-Opioid Receptor Antagonist TIPP Has an Important Effect on the Activity Profile

  摘要：

  The delta-opioid antagonist H-Tyr-Tic-Phe-Phe-OH (TIPP-OH) or its C-terminal amide analogue was systematically modified topologically by substitution of each amino acid residue by all stereoisomers of the corresponding beta-methyl amino acid. The potency and selectivity (delta- vs mu- and kappa-opioid receptor) were evaluated by radioreceptor binding assays. Agonist or antagonist potency were assayed in the mouse vas deferens and in the guinea pig ileum. In the TIPP analogues containing L-beta-methyl amino acids the influence on delta-receptor affinity and on delta-antagonist potency is limited, the [(2S,3R)-beta-MePhe(3)]TIPP-OH analogue being among the most potent delta-antagonists reported. In the D-beta-methyl amino acid series, the [D-beta-MeTic(2)] analogues are delta-selective antagonists whereas [D-Tic(2)]TIPP-NH2 is a delta-agonist. NMR studies did not indicate any influence of the beta-methyl substituent on the conformation of the Tic residue. The [(2R,3S)-beta-MePhe(3)]TIPP-NH2 is a potent delta-agonist, its C-terminal carboxylic acid analogue being more delta-selective but displaying partial agonism in both the delta- and mu-bioassay. These results constitute further examples of a profound influence of beta-methyl substitution on the potency, selectivity, and signal transduction properties of a peptide.

  DOI：

  10.1021/jm981011u