Ac-Phe-Val-OMe | 53842-46-9

• 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: Ac-Phe-Val-OMe
• 英文别名: N-Ac-L-Phe-L-Val methyl ester；methyl (2S)-2-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-3-methylbutanoate
• CAS: 53842-46-9
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: QBIRKQYTZFWPLE-GJZGRUSLSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  551.5±50.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ac-Phe-Val-OMe 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 Ac-Phe-Val-OH
  参考文献：
  名称：

  Design and synthesis of broad-Based mono- and bi- cyclic inhibitors of FIV and HIV proteases

  摘要：

  Based on the substrate transition state and our strategy to tackle the problem of drug resistance, a series of HIV/FIV protease (HIV/FIV PR) monocyclic inhibitors incorporating a 15- or 17-membered macrocycle with an equivalent P3 or P3' group and a unique unnatural amino acid, (2R, 3S)-3-amino-2-hydroxy-4-phenylbutyric acid, have been designed and synthesized. In addition, based on the structure of TL3 with small P3/P3' group, we have synthesized two conformationally restricted bicyclic inhibitors containing the macrocycle, which mimic the P1/P1'-P3/P3' tripeptide [Phe-Val-Ala] of TL3. We have found that the contribution of the macrocycle in our monocyclic inhibitors is important to the overall activity, but the ring size does not affect the activity to a significant extent. Several inhibitors that were developed in this work, exhibit low nanomolar inhibitory activity against the wild-type HIV/FIV PR and found to be highly effective against some drug-resistant as well as TL3-resistant mutants of HIV PRs. Compound 15, in particular, is the most effective cyclic inhibitor in hand to inhibit FIV replication in tissue culture at a concentration of 1.0 mug/mL (1.2 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00054-3
• 作为产物：
  描述：

  N-[(1S)-2-氯-2-氧代-1-(苯甲基)乙基]-氨基甲酸-9H-芴-9-甲酯 在 三氯化铝 、 sodium carbonate 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 8.0h， 生成 Ac-Phe-Val-OMe
  参考文献：
  名称：

  在 AlCl3/N,N-二甲基苯胺试剂系统中通过调节摩尔比对 N-Fmoc-氨基酸和 N-Fmoc-二肽甲酯的 α-氨基和羧基官能团进行选择性和化学选择性脱保护

  摘要：

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400321

文献信息

• Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis
  作者：Shouxin Liu、Yihua Yang、Xinwei Liu、Farhana K. Ferdousi、Andrei S. Batsanov、Andrew Whiting

  DOI：10.1002/ejoc.201300560

  日期：2013.9

  The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65–68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings

  已经研究了由芳基硼酸催化的氨基酸衍生物的直接酰胺化。相对于简单的胺-羧酸组合，该反应通常较慢，但通常在 65-68°C 下进行，避免了外消旋化。发现 3,4,5-三氟苯基硼酸和邻硝基苯基硼酸是最好的催化剂，但对于较慢的二肽形成，需要高催化剂负载量，并且发现了两种芳基硼酸之间有趣的协同催化作用。
• Study of the inf luence of the alkyl ester group in (S)-valinates on diastereoselectivity of their condensation with N-acetylphenylalanine by the mixed anhydride method
  作者：E. A. Zhdanova、N. Z. Solieva、L. Sh. Sadretdinova、M. A. Ezhikova、M. I. Kodess、V. P. Krasnov

  DOI：10.1007/s11172-006-0353-5

  日期：2006.5

  The dynamic kinetic resolution in the synthesis of alkyl N-acetylphenylalanyl (S)-valinates was studied by the mixed anhydride method. The structure of the ester group of the amino component appeared to exert no substantial effect on the diastereoselectivity of the reaction.

  采用混合酸酐法研究了烷基N-乙酰苯丙氨酰(S)-缬氨酸合成中的动态动力学拆分。氨基组分的酯基结构似乎对反应的非对映选择性没有实质性影响。
• Design and synthesis of broad-Based mono- and bi- cyclic inhibitors of FIV and HIV proteases
  作者：Chi Ching Mak、Ashraf Brik、Danica L Lerner、John H Elder、Garrett M Morris、Arthur J Olson、Chi-Huey Wong

  DOI：10.1016/s0968-0896(03)00054-3

  日期：2003.5

  Based on the substrate transition state and our strategy to tackle the problem of drug resistance, a series of HIV/FIV protease (HIV/FIV PR) monocyclic inhibitors incorporating a 15- or 17-membered macrocycle with an equivalent P3 or P3' group and a unique unnatural amino acid, (2R, 3S)-3-amino-2-hydroxy-4-phenylbutyric acid, have been designed and synthesized. In addition, based on the structure of TL3 with small P3/P3' group, we have synthesized two conformationally restricted bicyclic inhibitors containing the macrocycle, which mimic the P1/P1'-P3/P3' tripeptide [Phe-Val-Ala] of TL3. We have found that the contribution of the macrocycle in our monocyclic inhibitors is important to the overall activity, but the ring size does not affect the activity to a significant extent. Several inhibitors that were developed in this work, exhibit low nanomolar inhibitory activity against the wild-type HIV/FIV PR and found to be highly effective against some drug-resistant as well as TL3-resistant mutants of HIV PRs. Compound 15, in particular, is the most effective cyclic inhibitor in hand to inhibit FIV replication in tissue culture at a concentration of 1.0 mug/mL (1.2 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.
• Alternative and Chemoselective Deprotection of the ?-Amino and Carboxy Functions ofN-Fmoc-Amino Acid andN-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System
  作者：Maria�Luisa Di Gioia、Antonella Leggio、Adolfo Le Pera、Angelo Liguori、Francesca Perri、Carlo Siciliano

  DOI：10.1002/ejoc.200400321

  日期：2004.11

  The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N-dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)