Boc-Phe-Phe-Gly-OEt | 62307-54-4

• 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: Boc-Phe-Phe-Gly-OEt
• 英文别名: ethyl 2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]acetate
• CAS: 62307-54-4
• 化学式: C₂₇H₃₅N₃O₆
• 分子量: 497.591
• InChiKey: CUNQRVCNXGSOCO-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Phe-Gly-OEt 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以82%的产率得到N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine
  参考文献：
  名称：

  Lipkowski, Andrzej W.; Misicka, Aleksandra; Drabarek, Stefania, Polish Journal of Chemistry, 1981, vol. 55, # 4, p. 813 - 818

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 Boc-Phe-Phe-Gly-OEt
  参考文献：
  名称：

  Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues

  摘要：

  A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized. Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology and these were reacted with excess hydroxylamine in either ethanol or NN-dimethylformamide. The products were characterized by chromatographic methods, amino acid analysis and fast atom bombardment mass spectrometry. The inhibition of the degradation of the radiolabelled substrate desamino-[3-I-125-tyroSyl5]SP(5-11) ([(I-125)BH5]SP(5-11)) by these compounds in rat hypothalamus preparations was determined. The most potent inhibitors found were Boc-Phe-Phe-Phe-NHOH (12d, IC50 = 4-mu-M), Boc-Phe-Phe-Trp-NHOH (9, IC50 = 5-mu-M) and desamino-Tyr-Phe-Phe-Gly-NHOH (22, IC50 = 1.8-mu-M). A model describing the interaction of these compounds with the active site is proposed.

  DOI：

  10.1016/0223-5234(92)90001-h

文献信息

• Kainic acid as conformationally constrained glutamic acid analog in peptide synthesis
  作者：Florinda Artuso、Giovanni Sindona、Constantinos Athanassopoulos、George Stavropoulos、Dionissios Papaioannou

  DOI：10.1016/0040-4039(95)02000-f

  日期：1995.12

  A synthetic protocol is described which allows the incorporation of the γ-amide (Kan) and the γ-benzyl ester [Kai(Bzl)] and ether [Kol(Bzl)] of kainic acid (Kai) into peptide chains as exemplified with the synthesis of the substance P (SP) analogs [Kan5]-SP5−11, [Glp5. Kan6]-SP5−11. [Kan6]-SP6 11.[Glp5. Kai(Bzl)11]-SP5−11 and [Glp5. Kol(Bzl)11]-SP5−11.

  描述了一种合成方案，该方案允许将卡因酸（Kai）的γ-酰胺（Kan）和γ-苄基酯[Kai（Bzl）]和醚[Kol（Bzl）]掺入肽链，例如物质P（SP）类似物[Kan 5 ] -SP 5-11，[Glp 5。简6 ] -SP 5-11。[Kan 6 ] -SP 6 11。 [Glp 5。Kai（Bzl）11 ] -SP 5-11和[Glp 5。Kol（Bzl）11 ] -SP 5-11。
• HMDO-Promoted Peptide and Protein Synthesis in Ionic Liquids
  作者：Jianli Duan、Yao Sun、Hao Chen、Guofu Qiu、Haibing Zhou、Ting Tang、Zixin Deng、Xuechuan Hong

  DOI：10.1021/jo400797t

  日期：2013.7.19

  Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.
• Modelluntersuchungen zur papainkatalysierten Peptidsynthese im w��rig-organischen Zweiphasensystem
  作者：G�nter D�ring、Peter Kuhl、Hans-Dieter Jakubke

  DOI：10.1007/bf00905471

  日期：1981.10