Boc-Tyr-Pro-Phe-Phe-OBzl | 897959-54-5

• 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: Boc-Tyr-Pro-Phe-Phe-OBzl
• CAS: 897959-54-5
• 化学式: C₄₄H₅₀N₄O₈
• 分子量: 762.903
• InChiKey: WJQZMNIUQLBQLM-ZQWQDMLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  163.37
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-Pro-Phe-Phe-OBzl 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 5-[3-(5-{(S)-2-[(S)-2-({(S)-1-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-phenyl-propionylamino}-pentyl)-thioureido]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  6-N,N-Dimethylamino-2,3-naphthalimide:  A New Environment-Sensitive Fluorescent Probe in δ- and μ-Selective Opioid Peptides

  摘要：

  new environment-sensitive fluorophore, 6-N,N-(dimethylamino)-2,3-naphthalimide (6DMN) was introduced in the delta-selective opioid peptide agonist H-Dmt-Tic-Glu-NH2 and in the mu-selective opioid peptide agonist endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2). Environment-sensitive fluorophores are a special class of chromophores that generally exhibit a low quantum yield in aqueous solution but become highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. New fluorescent delta-selective irreversible antagonists (H-Dmt-Tic-Glu-NH-(CH2)(5)-CO-Dap(6DMN)-NH2 (1) and H-Dmt-Tic-Glu-Dap(6DMN)-NH2 ( 2)) were identified as potential fluorescent probes showing good properties for use in studies of distribution and internalization of delta receptors by confocal laser scanning microscopy.

  DOI：

  10.1021/jm060343t
• 作为产物：
  描述：

  TFA*H-Phe-Phe-OBzl 、 Boc-Tyr-Pro-OH 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以89%的产率得到Boc-Tyr-Pro-Phe-Phe-OBzl
  参考文献：
  名称：

  A new opioid designed multiple ligand derived from the μ opioid agonist endomorphin-2 and the δ opioid antagonist pharmacophore Dmt-Tic

  摘要：

  Opioid compounds with mixed mu agonist/delta antagonist properties could be used as analgesics with low propensity to induce tolerance and dependence. Here we report the synthesis of a new designed multiple ligand deriving from the p selective agonist endomorphin-2 and the delta selective antagonist pharmacophore Dmt-Tic. As predicted, the resulting bivalent ligand showed a p agonist/delta antagonist profile deriving fi-om the corresponding activities of each pharmacophore. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.047

文献信息

• Iron-Catalyzed C–H Alkylamination of Tyrosine Derivatives
  作者：Takahiro Yamada

  DOI：10.1021/acs.orglett.4c01764

  日期：2024.6.28

  method for the direct alkylamination of tyrosine derivatives via iron-catalyzed C–H amination has been developed. The method, using O-benzoyl-N,N-dialkylhydroxylamines as aminating agents, provides various C-amino-functionalized tyrosine derivatives in up to 77% yield. The utility of this method is showcased by its application to the direct introduction of drug molecules into tyrosine, facilitating access

  开发了一种通过铁催化 C-H 胺化对酪氨酸衍生物进行直接烷基胺化的有效方法。该方法使用O-苯甲酰基-N , N-二烷基羟胺作为胺化剂，以高达77%的产率提供各种C-氨基官能化的酪氨酸衍生物。该方法的实用性通过其将药物分子直接引入酪氨酸的应用来展示，有助于获得结构多样的氨基功能化酪氨酸衍生物。