Boc-Phe-Val-NH2 | 33900-19-5

• 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: Boc-Phe-Val-NH2
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 33900-19-5
• 化学式: C₁₉H₂₉N₃O₄
• 分子量: 363.457
• InChiKey: NWULLRLFRDVCFI-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110.52
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Val-NH2 在 三氟乙酸 作用下， 反应 1.0h， 以92%的产率得到H-Phe-Val-NH2*HCl
  参考文献：
  名称：

  Opioid Activities of Morphiceptin Analogs Derived from Human β-Casein

  摘要：

  合成了四种含有N端Tyr–Pro序列的四肽酰胺，它们可能是由人β-酪蛋白降解产生的可能与阿片受体结合的物质。当这些肽用于测试它们结合大鼠脑μ和δ阿片受体的能力时，仅H–Tyr–Pro–Phe–Val-NH2有活性，与来自牛β-酪蛋白的吗啡酰肽(H–Tyr–Pro–Phe–Pro–NH2)相比，它对μ受体具有60%的亲和力增加。它也像吗啡酰肽一样具有很高的μ选择性，μ/δ选择性比为285。其他三个类似物，H–Tyr–Pro–Ser–Phe–NH2、H–Tyr–Pro–Val–Arg–NH2 和 H–Tyr–Pro–Val–Pro–NH2，几乎完全无活性。这些结果表明，对于类似吗啡酰肽的四肽酰胺，在第3位存在Phe对于引发与μ阿片受体的结合活性至关重要。通过测量圆二色谱光谱进行的构象分析表明，四肽酰胺序列 Tyr–Pro–Xxx–Pro(或Val)–NH2 是与μ阿片受体相互作用的重要结构要求。

  DOI：

  10.1246/bcsj.63.1753
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 L-缬氨酰胺盐酸盐 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到Boc-Phe-Val-NH2
  参考文献：
  名称：

  Opioid Activities of Morphiceptin Analogs Derived from Human β-Casein

  摘要：

  合成了四种含有N端Tyr–Pro序列的四肽酰胺，它们可能是由人β-酪蛋白降解产生的可能与阿片受体结合的物质。当这些肽用于测试它们结合大鼠脑μ和δ阿片受体的能力时，仅H–Tyr–Pro–Phe–Val-NH2有活性，与来自牛β-酪蛋白的吗啡酰肽(H–Tyr–Pro–Phe–Pro–NH2)相比，它对μ受体具有60%的亲和力增加。它也像吗啡酰肽一样具有很高的μ选择性，μ/δ选择性比为285。其他三个类似物，H–Tyr–Pro–Ser–Phe–NH2、H–Tyr–Pro–Val–Arg–NH2 和 H–Tyr–Pro–Val–Pro–NH2，几乎完全无活性。这些结果表明，对于类似吗啡酰肽的四肽酰胺，在第3位存在Phe对于引发与μ阿片受体的结合活性至关重要。通过测量圆二色谱光谱进行的构象分析表明，四肽酰胺序列 Tyr–Pro–Xxx–Pro(或Val)–NH2 是与μ阿片受体相互作用的重要结构要求。

  DOI：

  10.1246/bcsj.63.1753

文献信息

• Polypeptides. Part XII. The preparation of 2-pyridyl esters and their use in peptide synthesis
  作者：A. S. Dutta、J. S. Morley

  DOI：10.1039/j39710002896

  日期：——

  amino-acid derivatives, and hydroxy-compounds) than the corresponding p-nitrophenyl esters. Evidence is presented that they are likely to be particularly useful in solid-phase peptide synthesis, and in the synthesis of O-peptides and depsipeptides.

  2-吡啶基的酯ñ -酰基氨基羧酸可从羧酸，2-羟基吡啶，并准备NN（仅“在吡啶-dicyclohexylcarbodi酰亚胺ñ在乙腈或二氯甲烷中形成-acylureas）。所述Ñ -t丁氧基-羰基-氨基甲酸2-吡啶基酯是大多结晶的，稳定的，并且在非极性溶剂相当对亲核试剂（胺，氨基-酯和酰胺更具反应性的，受阻氨基酸衍生物，和羟基化合物）比相应的对硝基苯酯。证据表明，它们可能在固相肽合成以及O肽和depsipeptide的合成中特别有用。
• Partially Modified Retro-Inverso Pseudopeptides as Non-natural Ligands for the Human Class I Histocompatibility Molecule HLA-A2
  作者：Gilles Guichard、Francine Connan、Roland Graff、Marina Ostankovitch、Sylviane Muller、Jean-Gérard Guillet、Jeannine Choppin、Jean-Paul Briand

  DOI：10.1021/jm9509511

  日期：1996.1.1

  Syntheses of a series of partially modified retro-inverso analogues of the antigenic peptide M58-66 derived from the influenza virus matrix protein are reported. The retro-inverso modification Psi(NH-CO) was obtained by replacement of two successive amino acid residues with a 2-substituted malonate derivative and gem-diaminoalkyl residue. The resulting compounds 1-8 were tested for their binding to the human histocompatibility class I molecule HLA-A2 in an assembly assay using lysates of peptide transporter-deficient cells T2. Specific peptide-dependent HLA-A2 assembly was revealed by an enzyme-linked immunosorbent assay. Significant HLA-A2 assembly was detected in the presence of analogues [gGly(58)-(S)mLeu(59)]-M58-66 (1a), [gGly(61)-(R,S)mPhe(62)]M58-66 (4), [gVal(63)-(R,S)mPhe(64)]M58-66 (6), and [gPhe(64)-(R,S)mAla(65)]M58-66 (7). The introduction of the retro-inverso modification between P2-P3, P3-P4, P5-P6, and P8-P9 (compounds 2, 3, 5, and 8, respectively) however led to a dramatic reduction in peptide binding to HLA-A2. Interestingly, compound 1a which contains modification between P1-P2 was found to be the most potent analogue, being able to retain the original HLA-A2 binding profile of the parent peptide M58-66. Taken together, these results and recent binding data obtained in the context of murine MHC class I molecule H-2K(d) suggest that the incorporation of peptide bond surrogates in MHC class I-restricted epitopes is a useful approach to design molecules having both increased stability and high MHC-binding capacity. Depending on their agonist or antagonist effects at the T-cell receptor, such non-natural MHC ligands are likely to find many applications in the development of peptide-based vaccines or as potential therapeutic agents in the treatment of allergies and autoimmune diseases.
• SAKAGUCHI, KAZUYASU;SAKAMOTO, HIROSHI;TSUBAKI, YOSHIKO;WAKI, MICHINORI;CO+, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 1753-1757
  作者：SAKAGUCHI, KAZUYASU、SAKAMOTO, HIROSHI、TSUBAKI, YOSHIKO、WAKI, MICHINORI、CO+

  DOI：——

  日期：——
• Opioid Activities of Morphiceptin Analogs Derived from Human β-Casein
  作者：Kazuyasu Sakaguchi、Hiroshi Sakamoto、Yoshiko Tsubaki、Michinori Waki、Tommaso Costa、Yasuyuki Shimohigashi

  DOI：10.1246/bcsj.63.1753

  日期：1990.6

  Four tetrapeptide amides with the N-terminal Tyr–Pro sequence were synthesized as possible opioid agonists that can be produced by degradation of human β-casein. When these peptides were tested for their ability to bind to the μ and δ opioid receptors in rat brain, only H–Tyr–Pro–Phe–Val-NH2 was active, showing the 60% increased affinity for the μ receptors as compared with morphiceptin (H–Tyr–Pro–Phe–Pro–NH2) derived from bovine β-casein. It was highly μ-selective, as well as morphiceptin, with the μ/δ-selectivity ratio of 285. Other three analogs, H–Tyr–Pro–Ser–Phe–NH2, H–Tyr–Pro–Val–Arg–NH2 and H–Tyr–Pro–Val–Pro–NH2, were almost completely inactive. These results suggested that, for the morphiceptin-like tetrapeptide amides, the presence of Phe at position 3 is essential to elicit an activity to bind to the μ opioid receptors. Conformational considerations by measuring the CD spectra indicated that the sequence of tetrapeptide amide Tyr–Pro–Xxx–Pro(or Val)–NH2 is an important structural requirement to interact with the μ opioid receptors.

  合成了四种含有N端Tyr–Pro序列的四肽酰胺，它们可能是由人β-酪蛋白降解产生的可能与阿片受体结合的物质。当这些肽用于测试它们结合大鼠脑μ和δ阿片受体的能力时，仅H–Tyr–Pro–Phe–Val-NH2有活性，与来自牛β-酪蛋白的吗啡酰肽(H–Tyr–Pro–Phe–Pro–NH2)相比，它对μ受体具有60%的亲和力增加。它也像吗啡酰肽一样具有很高的μ选择性，μ/δ选择性比为285。其他三个类似物，H–Tyr–Pro–Ser–Phe–NH2、H–Tyr–Pro–Val–Arg–NH2 和 H–Tyr–Pro–Val–Pro–NH2，几乎完全无活性。这些结果表明，对于类似吗啡酰肽的四肽酰胺，在第3位存在Phe对于引发与μ阿片受体的结合活性至关重要。通过测量圆二色谱光谱进行的构象分析表明，四肽酰胺序列 Tyr–Pro–Xxx–Pro(或Val)–NH2 是与μ阿片受体相互作用的重要结构要求。
• 1,3,5-Triazino Peptide Derivatives: Synthesis, Characterization, and Preliminary Antileishmanial Activity
  作者：Sherine N. Khattab、Hosam H. Khalil、Adnan A. Bekhit、Mohamed M. Abd El-Rahman、Beatriz G. de la Torre、Ayman El-Faham、Fernando Albericio

  DOI：10.1002/cmdc.201700770

  日期：2018.4.6

  All the synthesized peptide derivatives were analyzed by HPLC and fully characterized by IR spectroscopy, 1H and 13C NMR spectroscopy, elemental analysis, and mass spectrometry (MALDI TOF/TOF). A preliminary study of the antileishmanial activity of the 1,3,5‐triazinyl peptide derivatives revealed that four dipeptide amide derivatives showed higher antipromastigote or antiamastigote activity than the

  在溶液中和固相上制备了一个短的二肽，三肽和四肽文库，在N端带有s - triazine部分，在酰胺或乙酯C端都有一个。s-三嗪部分的其余两个位置被甲氧基，吗啉代或哌啶子基取代。所有合成的肽衍生物均通过HPLC进行分析，并通过红外光谱，1 H和13进行了全面表征13 C NMR光谱，元素分析和质谱（MALDI TOF / TOF）。对1,3,5-三嗪基肽衍生物的抗疟原虫活性的初步研究表明，四种二肽酰胺衍生物显示出比参比标准药物miltefosine更高的抗前鞭毛体或抗鞭毛体活性，而没有明显的急性毒性。