N-Cbz-Gly-Gly-Phe-Leu-OH | 69983-47-7

• 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: N-Cbz-Gly-Gly-Phe-Leu-OH
• 英文别名: Cbz-Gly-Gly-Phe-Leu-OH；(2S)-4-methyl-2-[[(2S)-3-phenyl-2-[[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetyl]amino]propanoyl]amino]pentanoic acid
• CAS: 69983-47-7
• 化学式: C₂₇H₃₄N₄O₇
• 分子量: 526.59
• InChiKey: UHTDFUVGRCNALT-VXKWHMMOSA-N

物化性质

• 沸点：
  895.6±65.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-Cbz-Gly-Gly-Phe-Leu-OH 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 脑啡肽
  参考文献：
  名称：

  Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent

  摘要：

  Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 +/- 1.10 X 104 M-1 and Delta G of -100.3 kJ mol-1 in comparison to a Ka 0.41 X 103 +/- 0.09 M-1 and Delta G of -19.2 +/- 0.06 kJ mol(-1) for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg(-1) dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.

  DOI：

  10.1021/acs.jmedchem.6b00134
• 作为产物：
  描述：

  甲基N-[(苄氧基)羰基]甘氨酰甘氨酸酸酯 在 氯甲酸乙酯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 26.5h， 生成 N-Cbz-Gly-Gly-Phe-Leu-OH
  参考文献：
  名称：

  Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent

  摘要：

  Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 +/- 1.10 X 104 M-1 and Delta G of -100.3 kJ mol-1 in comparison to a Ka 0.41 X 103 +/- 0.09 M-1 and Delta G of -19.2 +/- 0.06 kJ mol(-1) for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg(-1) dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.

  DOI：

  10.1021/acs.jmedchem.6b00134

文献信息

• 3-hydroxypropionitrile: A new reagent for carboxyl protection in peptide synthesis
  作者：P.K. Misra、S.A.N. Hashmi、W. Haq、S.B. Katti

  DOI：10.1016/s0040-4039(00)99443-7

  日期：1989.1
• MISRA, P. K.;HASHMI, S. A. N.;HAQ, W.;KATTI, S. B., TETRAHEDRON LETT., 30,(1989) N7, C. 3569-3572
  作者：MISRA, P. K.、HASHMI, S. A. N.、HAQ, W.、KATTI, S. B.

  DOI：——

  日期：——
• Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent
  作者：Palwinder Singh、Sukhmeet Kaur、Jagroop Kaur、Gurjit Singh、Rajbir Bhatti

  DOI：10.1021/acs.jmedchem.6b00134

  日期：2016.4.28

  Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 +/- 1.10 X 104 M-1 and Delta G of -100.3 kJ mol-1 in comparison to a Ka 0.41 X 103 +/- 0.09 M-1 and Delta G of -19.2 +/- 0.06 kJ mol(-1) for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg(-1) dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.