内吗啡肽 | 74135-04-9

• 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
• 中文名称: 内吗啡肽
• 英文名称: morphiceptin
• 英文别名: H-Tyr-Pro-Phe-Pro-NH2；Tyr-Pro-Phe-Pro-NH2；morphicetin；YPFP-NH2；(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide
• CAS: 74135-04-9
• 化学式: C₂₈H₃₅N₅O₅
• 分子量: 521.616
• InChiKey: LSQXZIUREIDSHZ-ZJZGAYNASA-N

物化性质

• 沸点：
  919.9±65.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Tyr-Pro-OEt hydrochloride 、 H-Phe-Pro-NH2*HCl 在 二异丙胺 作用下， 以 phosphate buffer 、 乙二醇 为溶剂， 反应 24.0h， 以40%的产率得到内吗啡肽
  参考文献：
  名称：

  Synthesis of Morphiceptin (Tyr-Pro-Phe-Pro-NH₂) by Dipeptidyl Aminopeptidase IV Derived from Aspergillus oryzae

  摘要：

  Morphiceptin (TYr-Pro-Phe-Pro-NH2), tetrapeptide, was synthesized using dipeptidyl aminopeptidase IV (DP IV, EC 3.4.14.5) derived from Aspergillus oryzae RIB 915 as a catalyst. Tyr-Pro-OEt was incubated with Phe-Pro-NH2 in the presence of DID IV under various. conditions of temperature, concentrations of ethylene glycol, pH, reaction time, and others. Morphiceptin was obtained at 40% yield under the optimal reaction conditions: substrate, 4 mM Tyr-Pro-OEt center dot HCl and 20 mM Phe-ProNH(2)center dot HCl; enzyme, DP IV, 0.275 nkat; solvent, 60% ethylene glycol containing 20 mM phosphate buffer at pH 7.0; amine, 4.2 mM diisopropylamine at 4 degrees C for 24 h. Amino group protection was unnecessary for synthesis of morphiceptin by DID IV.

  DOI：

  10.1021/jf050420d

文献信息

• Synthesis, biological evaluation and structural analysis of novel peripherally active morphiceptin analogs
  作者：Anna Adamska、Alicja Kluczyk、Maria Camilla Cerlesi、Girolamo Calo、Anna Janecka、Attila Borics

  DOI：10.1016/j.bmc.2016.02.034

  日期：2016.4

  ligand of the μ-opioid receptor (MOR). This study reports the synthesis and biological evaluation of a series of novel morphiceptin analogs modified in positions 2 or/and 4 by introduction of 4,4-difluoroproline (F2Pro) in l or d configuration. Depending on the fluorinated amino acid configuration and its position in the sequence, new analogs behaved as selective full MOR agonists showing high, moderate

  Morphiceptin（Tyr-Pro-Phe-Pro-NH 2）是一种四肽酰胺，是μ阿片受体（MOR）的选择性配体。这项研究报告了通过引入1或d构型的4,4-二氟脯氨酸（F 2 Pro）在2或/和4位修饰的一系列新型吗啡肽类似物的合成和生物学评估。取决于氟化氨基酸的构型及其在序列中的位置，新的类似物表现为选择性的完全MOR激动剂，显示出高，中或相对低的效力。最有效的类似物Tyr-F 2 Pro-Phe- d -F 2 Pro-NH 2，尽管效能低，但也能激活κ阿片受体（KOR）。对接研究以及与MOR激动剂复合物的高分辨率晶体学结构进行的结果比较表明，该化合物家族可能存在结构-活性关系。
• Synthesis of Morphiceptin (Tyr-Pro-Phe-Pro-NH₂) by Dipeptidyl Aminopeptidase IV Derived from <i>Aspergillus oryzae</i>
  作者：Toru Ota、Aki Itoh、Hiroshi Tachi、Keita Kudoh、Tatsuo Watanabe、Yuji Yamamoto、Tadahiro Tadokoro、Akio Maekawa

  DOI：10.1021/jf050420d

  日期：2005.7.1

  Morphiceptin (TYr-Pro-Phe-Pro-NH2), tetrapeptide, was synthesized using dipeptidyl aminopeptidase IV (DP IV, EC 3.4.14.5) derived from Aspergillus oryzae RIB 915 as a catalyst. Tyr-Pro-OEt was incubated with Phe-Pro-NH2 in the presence of DID IV under various. conditions of temperature, concentrations of ethylene glycol, pH, reaction time, and others. Morphiceptin was obtained at 40% yield under the optimal reaction conditions: substrate, 4 mM Tyr-Pro-OEt center dot HCl and 20 mM Phe-ProNH(2)center dot HCl; enzyme, DP IV, 0.275 nkat; solvent, 60% ethylene glycol containing 20 mM phosphate buffer at pH 7.0; amine, 4.2 mM diisopropylamine at 4 degrees C for 24 h. Amino group protection was unnecessary for synthesis of morphiceptin by DID IV.