Boc-Tyr-Val-OH | 906070-38-0

• 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: Boc-Tyr-Val-OH
• 英文别名: (2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-methylbutanoic acid
• CAS: 906070-38-0
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: QRDPXTLDMFHOOD-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  27.0
• 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：
  124.96
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-Val-OH 在 N-羟基-7-氮杂苯并三氮唑 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.25h， 生成 tert-butyl ((S)-1-(((S)-1-(((3S,6S,11R,E)-3-(4-hydroxybenzyl)-6-isopropyl-2,5,8-trioxo-1-oxa-4,7-diazacyclododec-9-en-11-yl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF BACKGROUND
  [FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本文披露了小分子钙蛋白酶调节剂、药物组合物、制备方法以及它们作为治疗剂的用途。这些治疗剂可用于治疗纤维化疾病或由此引起的继发性疾病状态或症状。这些小分子可以通过与CAPN1、CAPN2和/或CAPN9酶接触来抑制钙蛋白酶。

  公开号：

  WO2019217465A1
• 作为产物：
  描述：

  N-Boc-L-Tyr-L-ValOAll 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以78.9%的产率得到Boc-Tyr-Val-OH
  参考文献：
  名称：

  [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF BACKGROUND
  [FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本文披露了小分子钙蛋白酶调节剂、药物组合物、制备方法以及它们作为治疗剂的用途。这些治疗剂可用于治疗纤维化疾病或由此引起的继发性疾病状态或症状。这些小分子可以通过与CAPN1、CAPN2和/或CAPN9酶接触来抑制钙蛋白酶。

  公开号：

  WO2019217465A1

文献信息

• The role of terminal tyrosine residues in the formation of tripeptide nanotubes: a crystallographic insight
  作者：Sudipta Ray、Michael G.B. Drew、Apurba Kumar Das、Arindam Banerjee

  DOI：10.1016/j.tet.2006.05.042

  日期：2006.7

  Terminally protected acyclic tripeptides containing tyrosine residues at both termini self-assemble into nanotubes in crystals through various non-covalent interactions including intermolecular hydrogen bonds. The nanotube has an average internal diameter of 5 Å (0.5 nm) and the tubular ensemble is developed through the hydrogen-bonded phenolic-OH side chains of tyrosine (Tyr) residues [Org. Lett.2004

  在两个末端均含有酪氨酸残基的末端保护的无环三肽通过包括分子间氢键在内的各种非共价相互作用而自组装成晶体中的纳米管。纳米管的平均内径为5Å（0.5 nm），管状集合体是通过酪氨酸（Tyr）残基的氢键合酚羟基侧链形成的。来吧 2004年，6，4463]。我们已经合成并研究了几种三肽3 – 6探究酪氨酸残基在纳米管结构形成中的作用。这些肽在N末端或C末端仅具有一个Tyr残基，或者在末端具有一个或两个苯丙氨酸（Phe）残基。这些三肽不能以固态形式形成任何种类的纳米管结构。这些肽3 – 6的单晶X射线衍射研究清楚地表明，Boc-Tyr-X-Tyr-OMe序列中任何一个末端Tyr残基的取代（X = Val或Ile）都会破坏纳米管的形成。结构表明两个末端Tyr残基的存在对于纳米管的形成至关重要。
• Late‐Stage Halogenation of Peptides, Drugs and (Hetero)aromatic Compounds with a Nucleophilic Hydrazide Catalyst
  作者：Haripriyo Mondal、Subimal Patra、Shuvendu Saha、Tarak Nayak、Uddalak Sengupta、Modhu Sudan Maji

  DOI：10.1002/anie.202312597

  日期：2023.12.18

  A hydrazide catalyst is introduced for the late-stage halogenation of peptides, drugs and (hetero)aromatics with high efficiency and selectivity. The active site comprises the hydrazide group attached to a sulfonamide moiety, which facilitates the acceptance as well as delivery of halonium species from the N-halosuccinimide source to the substrates, thus featuring a cooperative interaction.

  引入酰肼催化剂，用于高效、选择性地对肽、药物和（杂）芳族化合物进行后期卤化。活性位点包含连接到磺酰胺部分的酰肼基团，这有利于卤鎓物质从N-卤代琥珀酰亚胺源到底物的接受和递送，从而具有协同相互作用的特征。
• 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.
• CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF BACKGROUND
  申请人：Blade Therapeutics, Inc.

  公开号：US20210253642A1

  公开（公告）日：2021-08-19

  Disclosed herein are small molecule calpain modulators, pharmaceutical compositions, preparation methods and their use as therapeutic agents. The therapeutic agents can be used for treating fibrotic disease or a resulting secondary disease state or condition. The small molecules can inhibit calpain through contact with CAPN1, CAPN2, and/or CAPN9 enzymes.