Boc-L-Trp-L-Ala-OMe | 63430-66-0

• 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-L-Trp-L-Ala-OMe
• 英文别名: Boc-Trp-Ala-OMe；methyl (2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 63430-66-0
• 化学式: C₂₀H₂₇N₃O₅
• 分子量: 389.451
• InChiKey: HZFZVKVJXSPTNY-LRDDRELGSA-N

物化性质

• 熔点：
  112-113 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  620.3±55.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-L-Trp-L-Ala-OMe 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 H2N-Trp-Ala-OMe
  参考文献：
  名称：

  Selective Inhibitors of the Serine Protease Plasmin:  Probing the S3 and S3‘ Subsites Using a Combinatorial Library

  摘要：

  A combinatorial library of 400 serine protease inhibitors with the general structure Cbz-X-aa-Trp-cyclohexanone-Trp-Y-aa-OH has been constructed. The library was synthesized on the solid phase using mix-and-split synthesis, where 20 different amino acids were incorporated at both the X-aa and Y-aa positions. These two positions correspond to the S3 and S3' subsites of the active site. Iterative deconvolution was used to identify hits from the library. The library was screened against four serine proteases: plasmin, kallikrein, thrombin, and trypsin. Seven inhibitors from the library that showed promising activities were resynthesized using solutionphase methods. Four of these compounds were good inhibitors of plasmin with IC50 values in the range of 2.7 - 3.6 mu M. The most potent of these inhibitors showed > 150-fold selectivity for plasmin when compared to the other three serine proteases.

  DOI：

  10.1021/jm050488k
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 33.0h， 生成 Boc-L-Trp-L-Ala-OMe
  参考文献：
  名称：

  Conditional changes enhanced production of bioactive metabolites of marine derived fungus Eurotium rubrum

  摘要：

  Metabolites of marine derived fungus Eurotium rubrum MPUC136 differed between cultivation on wheat medium and Czapek-Dox agar medium. Melanin synthesis inhibitory activity of crude extract of culture on wheat medium showed stronger activity than that of crude extract of culture on Czapek-Dox agar medium. A new diketopiperazine compound isoechinulin D (1) and eight reported diketopiperazines (2-9) were isolated from the crude extract of wheat medium. The structure of 1 was established using NMR, MS and IR methods. 2-5 inhibited melanogenesis using B16 melanoma cells (IC50 = 68, 2.4, 83, 9.1 mu M each). Structure-Activity-Relationships of diketopiperazines (1-10) indicated the importance of the prenyl groups at C-2, C-5 and C-7, the vinyl group at C-12 to C-25 and the sp(2) carbons at C-8 and C-9. Isolated compounds (1-9) were not or slightly observed from the extracts of Czapek-Dox agar medium by HPLC analysis, suggesting that different cultivation processes could affect metabolism and enhance bioactivities. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.017

文献信息

• 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO⁻ ) Universal Coupling Reagent for Synthesis in Solution
  作者：Justyna Fraczyk、Zbigniew J. Kaminski、Joanna Katarzynska、Beata Kolesinska

  DOI：10.1002/hlca.201700187

  日期：2018.1

  environmentally‐friendly N‐triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO− for peptide synthesis in solution, starting from Z‐, Fmoc‐, and Boc‐protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO− produced

  4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉的甲苯-4-磺酸酯（DMT / NMM / TSO - ），则廉价且环境友好的代表性构件Ñ磺酸的三叠氮基铵家族被发现是溶液中酰胺，酯和肽合成的非常有效的偶联剂。这项研究证实DMT / NMM / TSO的有用性-在溶液中的肽合成，从Z-，将Fmoc-，和起始Boc-保护的底物，以及不自然的构建块。用DMT / NMM / TsO进行肽合成-产量高，原油纯度高，外消旋化风险低。在所有情况下，都使用化学计量的试剂和标准的合成程序，而无需耗时的优化阶段或昂贵的色谱纯化。DMT / NMM / TSO -也被发现是用于使用片段偶联策略寡肽的合成中非常有用的。
• Copper‐Promoted N‐Arylation of the Indole Side Chain of Tryptophan Using Triarylbismuthines
  作者：Adrien Le Roch、Hwai‐Chien Chan、Alexandre Gagnon

  DOI：10.1002/ejoc.202000667

  日期：2020.9.30

  for the regioselective N‐arylation of the indole side chain of tryptophan using triarylbismuth reagents as the arylating agent is reported. The reaction is catalyzed by copper(II) acetate in the presence of an organic base. The protocol allows the installation of electron rich or poor aryl groups with substituents at any position, shows excellent scope and functional group compatibility, and retains

  报道了使用三芳基铋试剂作为芳基化剂的色氨酸吲哚侧链区域选择性N-芳基化的简单协议。在有机碱的存在下，该反应由乙酸铜（II）催化。该方案允许在任何位置安装带有取代基的富电子或弱芳基，显示出极好的范围和官能团相容性，并保留了立体中心的完整性。
• Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides
  作者：Benjamin Laroche、Xinjun Tang、Gaétan Archer、Riccardo Di Sanza、Paolo Melchiorre

  DOI：10.1021/acs.orglett.0c03735

  日期：2021.1.15

  report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor–acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical

  我们报告了一种用于含色氨酸 (Trp) 肽的化学选择性自由基功能化的光化学方法。该方法利用色氨酸单元和吡啶盐之间产生的电子供体-受体复合物的光活性。用弱光 (390 nm) 照射会在目标 Trp 氨基酸旁边产生自由基中间体，促进邻近驱动的自由基功能化。该协议对 Trp 残基比其他氨基酸具有高化学选择性，并且可以耐受生物相容性条件。
• 9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis
  作者：Samuel J. Aspin、Sylvain Taillemaud、Patrick Cyr、André B. Charette

  DOI：10.1002/anie.201606120

  日期：2016.10.24

  A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy‐to‐access 9‐silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing

  据报道，一种基本简单，温和且实用的肽键形成方法是采用化学计量的易于获得的9-二氟芴基二氯化物作为偶联剂。无需对氨基酸的羧酸或胺末端进行初步的预活化或精加工，就可以开发出一种通过空前的化学连接机制发挥作用的试剂，从而将两个偶联配偶体聚集在一起，然后再将其消除。因此以高收率和低至无差向异构化提供所需的酰胺或肽键。
• Data Science-Driven Analysis of Substrate-Permissive Diketopiperazine Reverse Prenyltransferase NotF: Applications in Protein Engineering and Cascade Biocatalytic Synthesis of (−)-Eurotiumin A
  作者：Samantha P. Kelly、Vikram V. Shende、Autumn R. Flynn、Qingyun Dan、Ying Ye、Janet L. Smith、Sachiko Tsukamoto、Matthew S. Sigman、David H. Sherman

  DOI：10.1021/jacs.2c06631

  日期：2022.10.26

  functionalization prevalent in the biosynthesis of a diverse array of biologically active bacterial, fungal, plant, and metazoan diketopiperazine (DKP) alkaloids. Toward the development of a unified strategy for biocatalytic construction of prenylated DKP indole alkaloids, we sought to identify and characterize a substrate-permissive C2 reverse prenyltransferase (PT). As the first tailoring event within the biosynthesis

  异戊二烯转移是一种早期碳氢键 (C–H) 功能化，普遍存在于多种具有生物活性的细菌、真菌、植物和后生动物二酮哌嗪 (DKP) 生物碱的生物合成中。为了开发异戊二烯化 DKP 吲哚生物碱生物催化构建的统一策略，我们试图鉴定和表征底物允许的 C2 反向异戊二烯基转移酶 (PT)。作为细胞毒性诺托酰胺代谢物生物合成中的第一个剪裁事件，PT NotF 催化短维胺 F 的 C2 反向异戊烯转移。解析 NotF 的晶体结构（与天然底物和异戊烯供体模拟物二甲基烯丙基 S-硫代二磷酸 (DMSPP) 形成复合物）揭示了一个大的，暴露于溶剂的活性位点，提示 NotF 可能具有非常广泛的底物范围。为了评估 NotF 的底物选择性，我们合成了一组 30 种空间和电子分化的色氨酸 DKP，其中大部分在合成有用的转化（2 至 >99%）中被 NotF 选择性异戊二烯化。该底物库的定量表示和描述性统计模型的开发提供了对