H-Tyr-D-Lys(Ac)-Phe-Gly-Tyr-Pro-Ser-NH2 | 1179539-53-7

• 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: H-Tyr-D-Lys(Ac)-Phe-Gly-Tyr-Pro-Ser-NH2
• 英文别名: (2S)-1-[(2S)-2-[[2-[[(2S)-2-[[(2R)-6-acetamido-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]hexanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
• CAS: 1179539-53-7
• 化学式: C₄₅H₅₉N₉O₁₁
• 分子量: 902.017
• InChiKey: UGWJTEBDBBDXLD-NWUFEJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  65
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  325
• 氢给体数：
  11
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-Fmoc-N’-烯丙氧基羰基-D-赖氨酸 、 Fmoc-甘氨酸 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 乙酸酐 、 Boc-O-叔丁基-L-酪氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 H-Tyr-D-Lys(Ac)-Phe-Gly-Tyr-Pro-Ser-NH2
  参考文献：
  名称：

  Discovery of Dermorphin-Based Affinity Labels with Subnanomolar Affinity for Mu Opioid Receptors

  摘要：

  A series of potent electrophilic affinity labels (IC50 = 0.1-5 nM) containing either a bromoacetamide or isothiocyanate based on the mu opioid receptor (MOR) selective peptide dermorphin were prepared. All four analogues exhibited wash resistant inhibition of [H-3]DAMGO binding at subnanomolar to nanomolar concentrations, suggesting that these analogues bind covalently to MOR. To our knowledge, these peptides are the highest affinity peptide-based affinity labels for MOR reported to date.

  DOI：

  10.1021/jm9007592

文献信息

• Discovery of Dermorphin-Based Affinity Labels with Subnanomolar Affinity for Mu Opioid Receptors
  作者：Bhaswati Sinha、Zhengyu Cao、Thomas F. Murray、Jane V. Aldrich

  DOI：10.1021/jm9007592

  日期：2009.12.10

  A series of potent electrophilic affinity labels (IC50 = 0.1-5 nM) containing either a bromoacetamide or isothiocyanate based on the mu opioid receptor (MOR) selective peptide dermorphin were prepared. All four analogues exhibited wash resistant inhibition of [H-3]DAMGO binding at subnanomolar to nanomolar concentrations, suggesting that these analogues bind covalently to MOR. To our knowledge, these peptides are the highest affinity peptide-based affinity labels for MOR reported to date.