Ac-Trp-Val-OMe | 248589-70-0

• 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-Trp-Val-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-acetamido-3-(1H-indol-3-yl)propanoyl]amino]-3-methylbutanoate
• CAS: 248589-70-0
• 化学式: C₁₉H₂₅N₃O₄
• 分子量: 359.425
• InChiKey: QOMCWVDXUGKRGU-IRXDYDNUSA-N

物化性质

• 沸点：
  652.3±55.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  100
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ac-Trp-Val-OMe 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 Ac-Trp-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：

  L-缬氨酸甲酯盐酸盐 、 N-乙酰-L-色氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Ac-Trp-Val-OMe
  参考文献：
  名称：

  含色氨酸的肽的选择性光氧化还原三氟甲基化

  摘要：

  描述了使用光氧化还原催化的色氨酸肽的可见光生物共轭。三氟甲基化在温和的，生物相容的和直接的条件下进行。使用这种策略，可以将三氟甲基结合到色氨酸残基中，具有出色的化学和位点选择性。

  DOI：

  10.1002/ejoc.201901572

文献信息

• Late-Stage Photoredox C–H Amidation of N-Unprotected Indole Derivatives: Access to <i>N</i>-(Indol-2-yl)amides
  作者：Yue Weng、Bo Ding、Yunqing Liu、Chunlan Song、Lo-Ying Chan、Chien-Wei Chiang

  DOI：10.1021/acs.orglett.1c00609

  日期：2021.4.2

  carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C–H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing

  N-未保护的吲哚的后期功能化可用于修饰低分子量药物和生物活性肽。吲哚羧酰胺在医药应用中很有价值，而具有相似结构的N-（吲哚-2-基）酰胺的制备仍然具有挑战性。本文中我们报道了可见光诱导的后期光氧化还原C–H酰胺化与N-未保护的吲哚和含色氨酸的肽，导致N的形成-（吲哚-2-基）酰胺衍生物。通过在室温下用绿色发光二极管照射，可以将含有吸电子基团的N-未保护的吲哚和芳氧基酰胺直接偶联至曙红Y作为光催化剂。机理研究和密度泛函理论计算表明，这种转变可能通过吲哚从PS *到PS •–循环的C–H氧化功能化而进行。该协议为N-未保护的吲哚衍生物的后期修饰标记和肽-药物结合提供了一个新的工具包。
• Determining the Diastereoselectivity of the Formation of Dipeptidonucleotides by NMR Spectroscopy
  作者：Olivia Doppleb、Jennifer Bremer、Maren Bechthold、Carolina Sánchez Rico、Daniela Göhringer、Helmut Griesser、Clemens Richert

  DOI：10.1002/chem.202101630

  日期：2021.9.24

  as building blocks. It is interesting to ask whether this is a coincidence or a consequence of the functional interplay of these biomolecules. One reaction that provides an opportunity to study this interplay is the formation of phosphoramidate-linked peptido RNA from amino acids and ribonucleotides in aqueous condensation buffer. Here we report how the diastereoselectivity of the first peptide coupling

  蛋白质由l-氨基酸组成，但核酸和大多数寡糖含有d-糖作为构建块。有趣的是要问这是巧合还是这些生物分子功能相互作用的结果。为研究这种相互作用提供机会的一个反应是在水性缩合缓冲液中由氨基酸和核糖核苷酸形成氨基磷酸酯连接的肽 RNA。在这里，我们报告了如何通过 NMR 光谱原位确定肽 RNA 途径的第一个肽偶联的非对映选择性。当氨基酸酯的外消旋混合物与 5'-氨基酸基核苷酸反应时，通过整合31 P-或1 H-NMR峰。发现同手性偶联产物d -Ser - d -Trp 的非对映体过量最高，氨基磷酸酯通过其d-核糖环与腺苷 5'-单磷酸相连。当用N控制反应时-乙酰氨基酸和缬氨酸甲酯在有机溶剂中运行，发现非对映选择性较低，非对映比≤62:38。因此探索性研究的结果表明，核糖核苷酸残基不仅促进了亲脂性氨基的偶联水介质中的酸，但也形成同手性二肽。此处描述的方法可用于搜索揭示同手性起源的其他立体选择性反应。
• Tandem Electrochemical Oxidative Azidation/Heterocyclization of Tryptophan‐Containing Peptides under Buffer Conditions
  作者：Yiyi Weng、Xiaobin Xu、Hantao Chen、Yiyang Zhang、Xianfeng Zhuo

  DOI：10.1002/anie.202206308

  日期：2022.10.10

  Manganese-catalyzed late-stage derivatization was used to construct azide-substituted tetrazolo[1,5-a]indole-containing peptides through a radical azidation/heterocyclization cascade. This electrochemical oxidative strategy could be conducted under mild, efficient, and environmentally friendly conditions in buffer solution.

  锰催化后期衍生化用于通过自由基叠氮化/杂环化级联构建叠氮取代的四唑并[1,5- a ]吲哚肽。这种电化学氧化策略可以在缓冲溶液中温和、高效、环保的条件下进行。
• Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides
  作者：Bo Ding、Yue Weng、Yunqing Liu、Chunlan Song、Le Yin、Jiafan Yuan、Yanrui Ren、Aiwen Lei、Chien-Wei Chiang

  DOI：10.1002/ejoc.201901572

  日期：2019.12.15

  visible‐light‐induced bioconjugation of tryptophan‐containing peptides using of photoredox catalysis is described. The trifluoromethylation proceeds under mild, biocompatible, and straightforward conditions. Using this strategy, the trifluoromethyl group could be incorporated into tryptophan residue with excellent chemo‐ and site‐selectivity.

  描述了使用光氧化还原催化的色氨酸肽的可见光生物共轭。三氟甲基化在温和的，生物相容的和直接的条件下进行。使用这种策略，可以将三氟甲基结合到色氨酸残基中，具有出色的化学和位点选择性。
• 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.