(S)-3-(4-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionic acid methyl ester | 65689-37-4

• 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: (S)-3-(4-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionic acid methyl ester
• CAS: 65689-37-4
• 化学式: C₂₇H₃₆N₂O₆
• 分子量: 484.593
• InChiKey: GZXMLWUISADVSI-GOTSBHOMSA-N

物化性质

• 沸点：
  647.8±55.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.25h， 以52%的产率得到Boc-Val-Tyr-OMe
  参考文献：
  名称：

  高通量竞争实验在天冬氨酸定向肽中酪氨酸残基的位点选择性修饰中的应用。

  摘要：

  在本文中，我们报告了铜催化的肽的位点选择性官能化，该肽采用天冬氨酸（Asp）作为天然的导向基序，将O-芳基化位点导向近端酪氨酸（Tyr）残基。通过在高通量反应阵列中进行的一系列竞争研究，确定了在Asp定向的Tyr修饰中对Tyr近端具有高选择性的有效条件。在许多情况下，包括肽-小分子杂交体，在靠近Tyr残基的O-芳基化反应中都实现了良好的位点选择性。

  DOI：

  10.1021/acs.joc.0c01147
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 、 2-氨基-3-(4-苯基甲氧基苯基)丙酸甲酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 (S)-3-(4-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionic acid methyl ester
  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

文献信息

• Solvent-free peptide synthesis assisted by microwave irradiation: environmentally benign synthesis of bioactive peptides
  作者：Amit Mahindra、Neha Patel、Nitin Bagra、Rahul Jain

  DOI：10.1039/c3ra46643d

  日期：——

  An efficient and facile, solvent-free peptide synthesis assisted by microwave irradiation, using DIC/HONB as the coupling reagent combination is reported. Key features of this original protocol are solvent-free synthesis, very short reaction time and scalability without affecting yield and purity. The versatility of the method was successfully demonstrated by synthesizing several biologically active

  报道了使用DIC / HONB作为偶联剂组合物的微波辐照辅助的有效且容易的，无溶剂的肽合成。该原始协议的关键特征是无溶剂合成，非常短的反应时间和可扩展性，而不会影响收率和纯度。通过以高纯度，高收率且不消旋地合成几种生物活性肽，成功证明了该方法的多功能性。