Boc-Phe-Phe-Phe-OMe | 53558-75-1

• 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-Phe-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoate
• CAS: 53558-75-1
• 化学式: C₃₃H₃₉N₃O₆
• 分子量: 573.689
• InChiKey: MLPXLARMCKAHOZ-KCHLEUMXSA-N

物化性质

• 熔点：
  174-175 °C(Solv: acetone (67-64-1); water (7732-18-5))
• 沸点：
  807.6±65.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-Phe-OMe 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以91.09%的产率得到Boc-L-Phe-L-Phe-L-Phe-OH
  参考文献：
  名称：

  Peptide based hydrogels for cancer drug release: modulation of stiffness, drug release and proteolytic stability of hydrogels by incorporating d-amino acid residue(s)

  摘要：

  这是一种针对抗癌药物释放定制设计的水凝胶的新颖示例。

  DOI：

  10.1039/c6cc01744d
• 作为产物：
  描述：

  BOC-L-苯丙氨酸琥珀酰亚胺酯 在 盐酸 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 2.66h， 生成 Boc-Phe-Phe-Phe-OMe
  参考文献：
  名称：

  对环境无害 肽 液体辅助球合成铣削：在亮脑啡肽的合成中的应用

  摘要：

  本文介绍了一种原始的方法 肽 避免毒性的键合成 溶剂和反应物。球-铣削在存在下，Boc保护的α-氨基酸N-羧基酸酐（Boc-AA-NCA）或Boc保护的α-氨基酸N-羟基琥珀酰亚胺酯（Boc-AA-OSu）的化学计量的NaHCO 3和最少量的EtOAc导致生成二甲苯五肽以有效和环保的方式。该方法已成功应用于亮脑啡肽的合成。

  DOI：

  10.1039/c3gc40302e

文献信息

• Intramolecular Ligation of Carbonyl Oxygen to Central Zinc in Synthetic Oligopeptide-Linked Zinc-Porphyrins
  作者：Hitoshi Tamiaki、Ayumu Kiyomori、Kazuhiro Maruyama

  DOI：10.1246/bcsj.67.2478

  日期：1994.9

  Oligopeptide-linked zinc-porphyrins were prepared (oligopeptide = –Phem–Alan–OMe and porphyrin = 5,15-diaryl-2,3,7,8,12,13,17,18-octaethylporphyrin). 1H NMR, IR, visible, and CD spectra of the synthetic molecule in a chlorinated methane (CDCl3 or CH2Cl2) showed that the carbonyl oxygen of the N-terminal amino acid of the linked peptide should ligate the central zinc metal in the molecule as the axial ligand to form a pentacoordinated zinc-porphyrin. The coordination of the zinc with the peptide framework changed the optical and electrical properties, indicating that such ligation might control the reactivity in biological metallotetrapyrrole–protein systems as well as the coordination to the peptide residue.

  通过寡肽连接的锌卟啉被制备出来（寡肽=–Phem–Alan–OMe，卟啉=5,15-二芳基-2,3,7,8,12,13,17,18-八乙基卟啉）。合成分子在氯化甲烷（CDCl3或CH2Cl2）中的1H NMR、IR、可见光和CD光谱显示，连接肽的N-末端氨基酸的羰基氧应该作为轴向配体配位到分子中的中心锌金属，形成五配位的锌卟啉。锌与肽骨架的配位改变了光学和电学性质，表明这种配位可能在生物金属四吡咯蛋白系统以及肽残基的配位中控制反应性。
• Fabrication of Luminescent CdS Nanoparticles on Short-Peptide-Based Hydrogel Nanofibers: Tuning of Optoelectronic Properties
  作者：Goutam Palui、Jayanta Nanda、Sudipta Ray、Arindam Banerjee

  DOI：10.1002/chem.200900149

  日期：2009.7.13

  the presence of CdS nanoparticles in a well‐defined array on the gel nanofibers. This is a convenient way to make organic nanofiber–inorganic nanoparticle hybrid nanocomposite systems. The size of the CdS nanoparticles remains almost same before and after deposition on the gel nanofiber. Photoluminescence (PL) measurement of the CdS nanoparticles upon deposition on the gel nanofibers shows a significant

  pH诱导的三种合成三肽在水介质中的自组装被用于固定发光的CdS纳米粒子。当在碱性pH值（pH 11.0-13.0）下在水性介质中凝胶化时，这些肽形成纳米原纤维网络结构，并且在凝胶纳米纤维上制备CdS纳米颗粒赋予这些凝胶发光特性。原子力显微镜，场发射扫描电子显微镜和高分辨率透射电子显微镜清楚地揭示了凝胶纳米纤维上以明确定义的阵列形式存在的CdS纳米粒子。这是制造有机纳米纤维-无机纳米颗粒杂化纳米复合材料系统的便捷方法。在凝胶纳米纤维上沉积前后，CdS纳米粒子的大小几乎保持不变。沉积在凝胶纳米纤维上后，CdS纳米颗粒的光致发光（PL）测量显示纳米颗粒的发射光谱发生了明显的蓝移，并且固定在不同的凝胶纳米原纤维上后，CdS纳米颗粒的PL间隙能量发生了显着变化。该发现表明，在凝胶纳米纤维上沉积时，可以调节CdS纳米粒子的光电性能，而无需改变纳米粒子的尺寸。
• Stereoselective reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters with Zn–MsOH
  作者：Naoki Kise、Shuji Takaoka、Masahiro Yamauchi、Nasuo Ueda

  DOI：10.1016/s0040-4039(02)01752-5

  日期：2002.10

  The reduction of N-hydroxy-α-imino esters with Zn–MsOH in THF afforded α-amino esters in high yields. The reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters prepared from l-phenylalanine and l-leucine di-, tri-, tetrapeptides gave the corresponding S-formed oligopeptide methyl esters in moderate diastereoselectivities.

  在THF中用Zn-MsOH还原N-羟基-α-亚氨基酯可高产率获得α-氨基酯。由1-苯丙氨酸和1-亮氨酸二-，三-，四肽制备的N-羟基-α-亚氨基羰基-寡肽甲酯的还原得到中等中等非对映选择性的相应的S-形成的寡肽甲酯。
• A Comprehensive Landscape for Fibril Association Behaviors Encoded Synergistically by Saccharides and Peptides
  作者：Rongying Liu、Ran Zhang、Long Li、Zdravko Kochovski、Lintong Yao、Mu-Ping Nieh、Yan Lu、Tongfei Shi、Guosong Chen

  DOI：10.1021/jacs.1c01951

  日期：2021.5.5
• Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues
  作者：A Ewenson、R Laufer、J Frey、M Chorev、Z Selinger、C Gilon

  DOI：10.1016/0223-5234(92)90001-h

  日期：1992.4

  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.