tert-butyl tert-butyloxycarbonyl-O-tert-butyl-L-tyrosyl-L-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-L-phenylalanyl-L-4-isothiocyanatophenylalaninate | 320782-54-5

• 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: tert-butyl tert-butyloxycarbonyl-O-tert-butyl-L-tyrosyl-L-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-L-phenylalanyl-L-4-isothiocyanatophenylalaninate
• 英文别名: tert-butyl (2S)-3-(4-isothiocyanatophenyl)-2-[[(2S)-2-[[(3S)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]-3-phenylpropanoyl]amino]propanoate
• CAS: 320782-54-5
• 化学式: C₅₁H₆₁N₅O₈S
• 分子量: 904.14
• InChiKey: DIXRDUNKXGXGMR-MXGQMUSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  65
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  197
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl tert-butyloxycarbonyl-O-tert-butyl-L-tyrosyl-L-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-L-phenylalanyl-L-4-isothiocyanatophenylalaninate 在 苯甲醚 、 三氟乙酸 作用下， 反应 1.0h， 以70%的产率得到L-tyrosyl-L-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-L-phenylalanyl-L-4-isothiocyanatophenylalanine
  参考文献：
  名称：

  Synthesis and Evaluation of Isothiocyanate-Containing Derivatives of the δ-Opioid Receptor Antagonist Tyr-Tic-Phe-Phe (TIPP) as Potential Affinity Labels for δ-Opioid Receptors

  摘要：

  Derivatives of the delta -opioid receptor-selective peptide antagonist H-Tyr-Tic-Phe-Phe-OH (TIPP) containing an isothiocyanate moiety at the para position of either Phe(3) or Phe(4) were prepared as potential affinity labels for delta -opioid receptors. The;synthesis was accomplished using a general solution-phase synthetic procedure which allows for introduction of affinity labeling groups late in the synthesis of a variety of small peptide substrates. The target peptides and their corresponding amines were then evaluated in radioligand binding experiments using Chinese hamster ovary (CHO) cells expressing delta- and mu -opioid receptors. The peptides [Phe-(P-NCS)(3)]TIPP (2) and [Phe(p-NCS)(4)]TIPP (4) showed affinity for delta -receptors comparable to the parent compound TIPP (IC50 = 12 and 5 nM, respectively, vs 6 nM for TIPP). Both peptides 2 and 4 were able to inhibit radioligand binding to d-receptors in a wash-resistant manner at a concentration of 10 nM. Therefore, the peptides [Phe(p-NCS)(3)]TIPP (2) and [Phe(p-NCS)(4)]-TIPP (4) represent two affinity labels that may prove useful in the study of delta -opioid receptors.

  DOI：

  10.1021/jm000345s
• 作为产物：
  描述：

  tert-butyl L-phenylalanyl-L-4-amino(9-fluorenylmethoxycarbonyl)phenylalaninate 在 哌啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 tert-butyl tert-butyloxycarbonyl-O-tert-butyl-L-tyrosyl-L-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-L-phenylalanyl-L-4-isothiocyanatophenylalaninate
  参考文献：
  名称：

  Synthesis and Evaluation of Isothiocyanate-Containing Derivatives of the δ-Opioid Receptor Antagonist Tyr-Tic-Phe-Phe (TIPP) as Potential Affinity Labels for δ-Opioid Receptors

  摘要：

  Derivatives of the delta -opioid receptor-selective peptide antagonist H-Tyr-Tic-Phe-Phe-OH (TIPP) containing an isothiocyanate moiety at the para position of either Phe(3) or Phe(4) were prepared as potential affinity labels for delta -opioid receptors. The;synthesis was accomplished using a general solution-phase synthetic procedure which allows for introduction of affinity labeling groups late in the synthesis of a variety of small peptide substrates. The target peptides and their corresponding amines were then evaluated in radioligand binding experiments using Chinese hamster ovary (CHO) cells expressing delta- and mu -opioid receptors. The peptides [Phe-(P-NCS)(3)]TIPP (2) and [Phe(p-NCS)(4)]TIPP (4) showed affinity for delta -receptors comparable to the parent compound TIPP (IC50 = 12 and 5 nM, respectively, vs 6 nM for TIPP). Both peptides 2 and 4 were able to inhibit radioligand binding to d-receptors in a wash-resistant manner at a concentration of 10 nM. Therefore, the peptides [Phe(p-NCS)(3)]TIPP (2) and [Phe(p-NCS)(4)]-TIPP (4) represent two affinity labels that may prove useful in the study of delta -opioid receptors.

  DOI：

  10.1021/jm000345s

文献信息

• Synthesis and Evaluation of Isothiocyanate-Containing Derivatives of the δ-Opioid Receptor Antagonist Tyr-Tic-Phe-Phe (TIPP) as Potential Affinity Labels for δ-Opioid Receptors
  作者：Dean Y. Maeda、Fred Berman、Thomas F. Murray、Jane V. Aldrich

  DOI：10.1021/jm000345s

  日期：2000.12.1

  Derivatives of the delta -opioid receptor-selective peptide antagonist H-Tyr-Tic-Phe-Phe-OH (TIPP) containing an isothiocyanate moiety at the para position of either Phe(3) or Phe(4) were prepared as potential affinity labels for delta -opioid receptors. The;synthesis was accomplished using a general solution-phase synthetic procedure which allows for introduction of affinity labeling groups late in the synthesis of a variety of small peptide substrates. The target peptides and their corresponding amines were then evaluated in radioligand binding experiments using Chinese hamster ovary (CHO) cells expressing delta- and mu -opioid receptors. The peptides [Phe-(P-NCS)(3)]TIPP (2) and [Phe(p-NCS)(4)]TIPP (4) showed affinity for delta -receptors comparable to the parent compound TIPP (IC50 = 12 and 5 nM, respectively, vs 6 nM for TIPP). Both peptides 2 and 4 were able to inhibit radioligand binding to d-receptors in a wash-resistant manner at a concentration of 10 nM. Therefore, the peptides [Phe(p-NCS)(3)]TIPP (2) and [Phe(p-NCS)(4)]-TIPP (4) represent two affinity labels that may prove useful in the study of delta -opioid receptors.