Valyl-tyrosine Methyl Ester | 54244-58-5

• 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: Valyl-tyrosine Methyl Ester
• 英文别名: N-L-valyl-L-tyrosine methyl ester；N-L-Valyl-L-tyrosin-methylester；Valinyl tyrosine methyl ester；methyl (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoate
• CAS: 54244-58-5
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: JHHYFVNEIHPLBN-STQMWFEESA-N

物化性质

• 熔点：
  113-115 °C
• 沸点：
  501.2±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Valyl-tyrosine Methyl Ester 在 sodium hydroxide 、 氢溴酸 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 反应 120.0h， 生成
  参考文献：
  名称：

  Martynov, V. F.; Anokhina, V. V.; Belokrylov, G. A., Journal of general chemistry of the USSR, 1989, vol. 59, # 10, p. 2122 - 2128

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Val-Tyr-OMe 在 三氟乙酸 作用下， 反应 1.0h， 生成 Valyl-tyrosine Methyl Ester
  参考文献：
  名称：

  模仿大环氨基酸的β链：具有抗病毒活性的蛋白酶抑制剂的模板。

  摘要：

  报道了新的氨基酸，其中组分大环被限制为模仿锁定在β链构象中的三肽。新型氨基酸涉及被N和C末端均官能化的大环，从而能够在任一末端添加附件以修饰受体亲和力，选择性或膜通透性。我们显示本文的循环是HIV-1蛋白酶抑制剂内的有效模板。源自这种双官能化环状模板的十一种化合物是HIV-1蛋白酶的有效抑制剂（Ki 0.3-50 nM； pH 6.5，I = 0.1 M）。与包含氨基酸的正常肽不同，这些含大环化合物中的五种是有效的抗病毒剂，具有针对人类MT2细胞中HIV-1复制的亚微摩尔潜能（IC（50）170-900 nM）。最活跃的抗病毒药是最亲脂的，计算值LogD（6.5）>或=4。所有分子均具有构象受限的17元大环，该环在结构上模仿三肽段（Xaa）-（Val / Ile）-（Phe / Tyr）。扩展构象的肽底物。两个反酰胺键和对位取代的芳环的存在可防止分子内氢键并将大环固定在延伸的构象中。类似地

  DOI：

  10.1021/jm010414i

文献信息

• Histamine H3 receptor antagonists with peptidomimetic (keto)piperazine structures to inhibit Aβ oligomerisation
  作者：Markus Falkenstein、David Reiner-Link、Aleksandra Zivkovic、Ian Gering、Dieter Willbold、Holger Stark

  DOI：10.1016/j.bmc.2021.116462

  日期：2021.11

  build toxic oligomers. Design of disease modifying multi target directed ligand (MTDL) has been performed, which disable PPI on the one hand and on the other hand, act as procognitive antagonists at the histamine H3 receptor (H3R). The synthetized compounds are structurally based on peptidomimetic amino acid-like structures mainly as keto, diketo-, or acyl variations of a piperazine moiety connected to

  阿尔茨海默病 (AD) 是最突出的神经退行性疾病，具有很高的医疗需求。蛋白质-蛋白质-相互作用 (PPI) 相互作用在 AD 中具有关键作用，其中 β-淀粉样蛋白结构 (Aβ) 构建有毒低聚物。已经进行了疾病修饰多靶点定向配体 (MTDL) 的设计，其一方面禁用 PPI，另一方面作为组胺 H 3受体 (H 3 R) 的促认知拮抗剂。合成的化合物在结构上基于肽模拟氨基酸样结构，主要是与 H 3 R 药效团连接的哌嗪部分的酮基、二酮基或酰基变体。它们中的大多数在 H 3处表现出低纳摩尔亲和力R 和一些对 Aβ-单体具有良好亲和力的物质。所描述的结构-活性关系 (SAR) 为 MTDL 提供了新的可能性，其优化的配置文件结合了 AD 中的症状和潜在因果治疗方法。
• Synthesis of a Protected Heptapeptide Related to the Histidine Analogue of Hypertensin II
  作者：DIMITRIOS THEODOROPOULOS

  DOI：10.1038/1841634a0

  日期：1959.11

  HYPERTENSIN II or isoleucine hypertensin II, a pressor peptide with the amino-acid sequence Asp.Arg.Val.Tyr.Is.His.Pro.Phe. has been synthesized along classical lines by two groups of investigators1.

  高血压素II或异亮氨酸高血压素II是一种具有氨基酸序列Asp.Arg.Val.Tyr.Is.His.Pro.Phe的升压肽，已被两个研究组按照经典方法合成。
• Synthese eines hochwirksamen Hypertensin II-amids (L-Asparaginyl-L-arginyl-L-valyl-L-tyrosyl-L-isoleucyl-L-histidyl-L-prolyl-L-phenylalanin)
  作者：W. Rittel、B. Iselin、H. Kappeler、B. Riniker、R. Schwyzer

  DOI：10.1002/hlca.19570400317

  日期：——

  described. The highly purified octapeptide is 5 to 10 times as active as noradrenaline on the blood pressure of the rat in the experimental set-up of Peart9), and 2 to 4 times as active as Val5- hypertensin I, isolated from bovine plasma3).

  描述了Ileu 5-高血压蛋白II-Asp-β-酰胺，L-天冬酰胺基-L-精氨酰基-L-戊基-L-酪氨酰基-L-异亮氨酰基-L-组氨酸-L-脯氨酰基-L-苯丙氨酸的合成。在Peart 9的实验装置中，高度纯化的八肽在大鼠血压上的活性是去甲肾上腺素的5到10倍，是从牛血浆3中分离出来的Val 5-高血压I的2到4倍。）。
• Development of tripeptidyl farnesyltransferase inhibitors
  作者：Hee-Yoon Lee、Jeong-Hun Sohn、Byoung-Mog Kwon

  DOI：10.1016/s0960-894x(02)00227-5

  日期：2002.6

  The first example of tripeptide inhibitors of farnesyltransferase with sub-micromolar inhibition activity was developed based on the fact that CVFM is not a substrate for farnesyltransferase. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Structures, Sensory Activity, and Dose/Response Functions of 2,5-Diketopiperazines in Roasted Cocoa Nibs (<i>Theobroma cacao</i>)
  作者：Timo Stark、Thomas Hofmann

  DOI：10.1021/jf051313m

  日期：2005.9.1

  The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and independent synthesis. Among these 25 compounds, 13 cis-configured diketopiperazines, namely, CYCIO(L-IIe-L-Phe), CYCIO(L-Val-L-Leu), CYCIO(L-Pro-L-Pro), CYCIO(L-IIe-L-Pro), CYCIO(L-Val-L-Tyr), CYCIO(L-Ala-L-Tyr), CYCIO(L-Phe-L-Ser), CYCIO(L-Ala-L-IIe), CYCIO(L-LeU-L-Phe), cyclo(L-Pro-L-Val), CYCIO(L-Pro-L-Thr), CYCIO(L-PrO-L-Tyr), and CYCIO(L-Val-L-Val) were identified for the first time in cocoa. In addition, the taste recognition thresholds for the metallic as well as the bitter taste of the diketopiperazines were determined, and after quantitative analysis by using two diastereomeric diketopiperazines as the internal standards, the sensory impact of the diketopiperazines was evaluated on the basis of their close-over-threshold (DoT) factors calculated as the ratio of the concentration and the threshold concentration of a compound. These data revealed DoT factors above 1.0 exclusively for cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Val-L-Leu), cis-cyclo(L-Ala-L-IIe), cis-cyclo(L-Ala-L-Leu), and cis-cyclo(L-IIe-L-Pro), whereas all of the other diketopiperazines were present below their individual bitter taste threshold concentrations and should therefore not contribute to the cocoa taste. Because the DoT factors do not consider the nonlinear relationship between the concentration and gustatory response of an individual compound, we, for the first time, report on the recording of dose/response functions describing the human bitter taste perception of diketopiperazines more precisely.