Boc-L-Tyr-L-Val-OMe | 406680-79-3

• 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-L-Tyr-L-Val-OMe
• 英文别名: methyl (tert-butoxycarbonyl)-L-tyrosyl-L-valinate；Boc-Tyr-Val-OMe；Boc-Tyr-Val-OCH₃；t-Butyloxycarbonyl-tyrosinyl-valine methyl ester；methyl (2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-methylbutanoate
• CAS: 406680-79-3
• 化学式: C₂₀H₃₀N₂O₆
• 分子量: 394.468
• InChiKey: QLNUJBNBWARMIA-HOTGVXAUSA-N

物化性质

• 沸点：
  587.3±50.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-L-Tyr-L-Val-OMe 在 盐酸 、 lithium hydroxide 、 四溴化碳 、 四丁基溴化铵 、 caesium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.5h， 生成 (10S,13S)-13-Amino-10-isopropyl-2,5-dioxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-9,12-dione; hydrochloride
  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 在 盐酸 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.25h， 生成 Boc-L-Tyr-L-Val-OMe
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors

  摘要：

  Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50 = 2.51 +/- 0.2 +/- mu M) showed similar inhibitory effect compared with control compound Bestatin (IC50 = 6.25 +/- 0.4 mu M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.

  DOI：

  10.3109/14756366.2012.680062

文献信息

• Copper‐Promoted O‐Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines
  作者：Adrien Le Roch、Martin Hébert、Alexandre Gagnon

  DOI：10.1002/ejoc.202000790

  日期：2020.9.7

  for the O‐arylation of the side chain of tyrosine using triarylbismuth reagents is reported. The reaction is performed in dichloromethane under oxygen at 50 °C in the presence of pyridine, is promoted by copper diacetate, shows excellent scope and functional group tolerance, and retains the integrity of the chiral center. The reactivity of other amino acids possessing a nucleophilic side chain under these

  报道了使用三芳基铋试剂对酪氨酸侧链进行O-芳基化的方法。该反应在吡啶存在下于氧气中于50°C的氧气中于二氯甲烷中进行，由二乙酸铜促进，显示出极好的范围和官能团耐受性，并保留了手性中心的完整性。研究了在这些条件下具有亲核侧链的其他氨基酸的反应性。可以实现含酪氨酸的二肽和三肽的O-酰化。
• Synthetic C6‐Functionalized Aminoflavin Catalysts Enable Aerobic Bromination of Oxidation‐Prone Substrates
  作者：Alexandra Walter、Golo Storch

  DOI：10.1002/anie.202009657

  日期：2020.12.7

  functional groups in the peptide environment of the flavin cofactor. We report synthetic flavin catalysts that contain C-6 amino modifications at the isoalloxazine core and are consequently capable of mediating halogenations outside the peptide surrounding. The catalysts are competent in selective, biomimetic bromination of oxidation-prone phenols, flavones, and flavanones using a halide salt in combination

  黄酮酶通过氢过氧化物中间体催化氧化，这是由分子O 2活化引起的。这些反应（例如羟基化和卤化）取决于黄素辅因子在肽环境中官能团的附加催化活性。我们报告了合成的黄素催化剂，其在异四恶嗪核心处含有C-6氨基修饰，因此能够在肽周围的肽外介导卤化作用。该催化剂具有在可见光照射下，结合卤化物盐和草酸2，6-lut啶鎓作为黄素还原剂，对易氧化的酚，黄酮和黄烷酮进行选择性，仿生溴化的能力。我们的研究显示了堆积的双黄素的有益作用，以及黄素修饰物的催化活性。
• Ru‐Catalyzed C−H Hydroxylation of Tyrosine‐Containing Di‐ and Tripeptides toward the Assembly of L‐DOPA Derivatives
  作者：Paula Andrade‐Sampedro、Jon M. Matxain、Arkaitz Correa

  DOI：10.1002/adsc.202200234

  日期：2022.6.21

  C(sp2)−H hydroxylation of a collection of Tyr-containing di- and tripeptides featuring the use of a carbamate as a removable directing group and PhI(OCOCF3)2 (PIFA) as oxidant. This air-compatible tagging technique is reliable, scalable and provides access to L-DOPA (L-3,4-dihydroxyphenylalanine) peptidomimetics in a racemization-free fashion. Density Functional Theory calculations support a Ru(II)/Ru(IV)

  开发用于肽框架内氨基酸后期修饰的催化工具是一项至关重要的具有挑战性的任务。在此，我们报道了一系列含 Tyr 的二肽和三肽的 Ru 催化 C( sp 2 )-H 羟基化反应，其特点是使用氨基甲酸酯作为可去除的导向基团和 PhI(OCOCF 3 ) 2 (PIFA) 作为氧化剂. 这种与空气兼容的标记技术可靠、可扩展，并以无消旋的方式提供对 L-DOPA（L-3,4-二羟基苯丙氨酸）肽模拟物的访问。密度泛函理论计算支持 Ru(II)/Ru(IV) 催化循环。
• Highly Sterically Hindered Peptide Bond Formation between α,α-Disubstituted α-Amino Acids and <i>N</i>-Alkyl Cysteines Using α,α-Disubstituted α-Amidonitrile
  作者：Xiaoling Wang、Jing Li、Yujiro Hayashi

  DOI：10.1021/jacs.2c02993

  日期：2022.6.15

  sterically hindered peptides, research on peptides bearing an amide bond between an α,α-disubstituted α-amino acid and an N-alkyl α-amino acid remains underexplored because of the lack of an efficient synthetic approach. Herein, we describe a high-yielding synthetic method to access such extremely sterically hindered peptide bonds between amino acids. The reaction takes place between a peptide with an α,α-disubstituted

  肽和蛋白质在学术界和工业界的许多领域引起了极大的关注。将不常见的氨基酸如 α,α-二取代的 α-氨基酸或N-烷基 α-氨基酸引入正常的肽骨架中是一种广泛利用且有用的工具，可用于修饰诸如构象、生物活性和药理概况。尽管对空间位阻肽很感兴趣，但对在 α,α-二取代的 α-氨基酸和N之间带有酰胺键的肽的研究由于缺乏有效的合成方法，-烷基α-氨基酸仍未得到充分探索。在这里，我们描述了一种高产合成方法来获得氨基酸之间这种极度空间位阻的肽键。该反应发生在具有 α,α-二取代的 α-酰胺腈的肽和具有N-烷基半胱氨酸的第二肽之间，无需偶联剂。
• Aqueous C–H aminomethylation of phenols by iodine catalysis
  作者：Zhi-Hua Zhou、Ben Wang、Yao Ding、Teck-Peng Loh、Jie-Sheng Tian

  DOI：10.1039/d2cc05746h

  日期：——

  transition-metal-free strategy regarding an iodine–sodium percarbonate catalysis to achieve the ortho-aminomethylation of phenols in aqueous media has been developed. This method can effectively broaden a wide range of phenols, tolerate sensitive functional groups, and achieve the late-stage functionalization of ten functional molecules that contain phenolic structures.

  已经开发了一种无过渡金属的策略，该策略涉及碘 - 过碳酸钠催化以实现水性介质中酚类的邻氨基甲基化。该方法可有效拓宽广泛的酚类化合物，耐受敏感的官能团，实现10个含酚结构的功能分子的后期功能化。