Z-L-Tyr(Bu-t)-Gly-Gly-OH | 62565-67-7

• 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: Z-L-Tyr(Bu-t)-Gly-Gly-OH
• 英文别名: Z-Tyr(Bu^t)-Gly-Gly-OH；Cbz-Tyr(tBu)-Gly-Gly-OH；2-[[2-[[(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetyl]amino]acetic acid
• CAS: 62565-67-7
• 化学式: C₂₅H₃₁N₃O₇
• 分子量: 485.537
• InChiKey: YOGJDQXLGJPHLW-FQEVSTJZSA-N

物化性质

• 沸点：
  807.6±65.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Z-L-Tyr(Bu-t)-Gly-Gly-OH 在 palladium on activated charcoal N-甲基吗啉 、 sodium hydroxide 、 氢气 、 ammonium formate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.17h， 生成 (N,N-dipropyl,Leu⁵)enkephalin
  参考文献：
  名称：

  N,N-Dialkylated leucine enkephalins as potential .delta. opioid receptor antagonists

  摘要：

  A series of N,N-dialkylated leucine enkephalins were prepared in order to study the effect of substitution on antagonist activity at the delta opioid receptor. The target peptides 1-7 were evaluated in the mouse vas deferens (MVD) and guinea pig ileum (GPI) at 1 microM. All of the compounds except [N,N-di-2-phenethyl,Leu5]enkephalin (7) showed antagonist activity in the MVD against the delta receptor agonist [D-Ala2,D-Leu5]enkephalin. The most potent congener, [N,N-dibenzyl,Leu5]enkephalin (3), was 2.5-fold more potent than [N,N-diallyl,Leu5]enkephalin (1). None of the compounds at 1 microM showed any antagonist activity against agonists for other receptor types. The N,N-di-2-phenethyl (7) and N,N-dioctyl (6) analogues showed significant agonist activity at 1 microM in the MVD.

  DOI：

  10.1021/jm00390a005
• 作为产物：
  描述：

  O-(叔丁基)-N-[(苯甲氧基)羰基]-L-酪氨酸 在 N-甲基吗啉 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 生成 Z-L-Tyr(Bu-t)-Gly-Gly-OH
  参考文献：
  名称：

  N,N-Dialkylated leucine enkephalins as potential .delta. opioid receptor antagonists

  摘要：

  A series of N,N-dialkylated leucine enkephalins were prepared in order to study the effect of substitution on antagonist activity at the delta opioid receptor. The target peptides 1-7 were evaluated in the mouse vas deferens (MVD) and guinea pig ileum (GPI) at 1 microM. All of the compounds except [N,N-di-2-phenethyl,Leu5]enkephalin (7) showed antagonist activity in the MVD against the delta receptor agonist [D-Ala2,D-Leu5]enkephalin. The most potent congener, [N,N-dibenzyl,Leu5]enkephalin (3), was 2.5-fold more potent than [N,N-diallyl,Leu5]enkephalin (1). None of the compounds at 1 microM showed any antagonist activity against agonists for other receptor types. The N,N-di-2-phenethyl (7) and N,N-dioctyl (6) analogues showed significant agonist activity at 1 microM in the MVD.

  DOI：

  10.1021/jm00390a005

文献信息

• A Simple and Convenient Method for the Synthesis of Iminomethylene Analogs of Peptides
  作者：Hidekazu Oyamada、Masaaki Ueki

  DOI：10.1246/bcsj.60.267

  日期：1987.1

  improving the conditions for the selective reduction of the peptide bond of N-protected dipeptide esters by borane. Among the ester residues investigated, the t-butyl ester gave the best result. During reactions no racemization occurred. [L-Pheψ[CH2–NH]L-Leu4−5]leucineenkephalin was synthesized in good yield starting from N-benzyloxycarbonyl-L-phenylalanyl-L-leucine t-butyl ester.

  研究了合成部分肽键被其他等排键取代的假肽，以获得长效肽药物，并研究肽与生物活性的构效关系。通过改进硼烷选择性还原 N 保护的二肽酯的肽键的条件，建立了一种简单方便的合成假 [CH2–NH]肽的方法。在所研究的酯残基中，叔丁酯的结果最好。在反应过程中没有发生外消旋化。[L-Pheψ[CH2-NH]L-Leu4-5]亮氨酸脑啡肽以N-苄氧羰基-L-苯丙氨酰基-L-亮氨酸叔丁酯为原料，以良好的收率合成。
• [EN] SELECTIVE CASPASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS SÉLECTIFS DES CASPASES ET LEURS UTILISATIONS
  申请人：NEW WORLD LAB INC

  公开号：WO2010133000A1

  公开（公告）日：2010-11-25

  The present invention relates to compounds of Formula I, II, IVC, VIIIC, IXC, or XC and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds for the selective inhibition of one or more caspases. Also described are methods where the compounds of Formula I, II, IVC, VIIIC, IXC, or XC are used in the prevention and/or treatment of various diseases and conditions in subjects, including caspase-mediated diseases such as sepsis, myocardial infarction, ischemic stroke, spinal cord injury (SCI), traumatic brain injury (TBI) and neurodegenerative disease (e.g. multiple sclerosis (MS) and Alzheimer's, Parkinson's, and Huntington's diseases). Processes for synthesizing tripeptides are provided.