N-tert-butoxycarbonyl-D-tryptophyl-L-leucine methyl ester | 128719-24-4

• 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: N-tert-butoxycarbonyl-D-tryptophyl-L-leucine methyl ester
• 英文别名: methyl (tert-butoxycarbonyl)-D-tryptophyl-L-leucinate；Boc-dWL-OMe；Boc-D-Trp-Leu-OMe；methyl (2S)-2-[[(2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoate
• CAS: 128719-24-4
• 化学式: C₂₃H₃₃N₃O₅
• 分子量: 431.532
• InChiKey: QJOONLXKWKZYEX-MOPGFXCFSA-N

物化性质

• 沸点：
  637.3±55.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  N-tert-butoxycarbonyl-D-tryptophyl-L-leucine methyl ester 在 盐酸 、 1-羟基苯并三唑 、 1,2-乙二硫醇 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-butoxycarbonyl-D-phenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester
  参考文献：
  名称：

  Dutta, Anand S; Cormley, James J; McLachlan, Peter F, Journal of Chemical Research, Miniprint, 1990, # 1, p. 101 - 170

  摘要：

  DOI：
• 作为产物：
  描述：

  D-色氨酸 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 N-tert-butoxycarbonyl-D-tryptophyl-L-leucine methyl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor

  摘要：

  Taking the tripeptide D-Trp-Arg-Leu-NH2 as a lead for a Xenopus laevis skin-melanocortin (MC) receptor antagonist, thirteen non-peptidic compounds were synthesized and biologically evaluated at Xenopus laevis melanophores. Six competitive antagonists (shown by Schild analysis) and one partial agonist were identified with moderate activity (IC50: 5-10 muM). Tryptophanamides with aliphatic side chains were inactive whereas basic residues restored activity. Introducing an imidazole residue yielded partial agonist activity (EC50: 32 muM). Interestingly, constraining the inactive S-tryptophan-isoamylamide to a beta-carboline ring yielded an MC receptor antagonist (42). The specificity for MC receptors was tested at various G-protein coupled receptors. In conclusion, the synthesis of non-peptidic MC receptor antagonists is described which may serve as lead compounds for further studies. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00062-x

文献信息

• Aerobic, Diselenide-Catalyzed Redox Dehydration: Amides and Peptides
  作者：Srirama Murthy Akondi、Pavankumar Gangireddy、Thomas C. Pickel、Lanny S. Liebeskind

  DOI：10.1021/acs.orglett.7b03620

  日期：2018.2.2

  At 2.5 mol % loadings using reaction temperatures between 30–55 °C, ortho-functionalized diaryl diselenides are highly effective organocatalytic oxidants for aerobic redox dehydrative amidic and peptidic bond formation using triethyl phosphite as a simple terminal reductant. This simple-to-perform organocatalytic reaction relies on the ability of selenols to react directly with dioxygen in air without

  在反应温度为30-55°C的条件下，负载量为2.5 mol％时，邻官能化的二芳基二硒化物是高效的有机催化氧化剂，可利用亚磷酸三乙酯作为简单的末端还原剂来形成需氧氧化还原脱水的酰胺和肽键。这种简单易行的有机催化反应依赖于硒醇与空气中的双氧直接反应而不依赖金属催化剂的能力。它代表了开发通用，经济且良性的催化氧化还原脱水方案的重要一步。
• Dutta, Anand S; Cormley, James J; McLachlan, Peter F, Journal of Chemical Research, Miniprint, 1990, # 1, p. 101 - 170
  作者：Dutta, Anand S、Cormley, James J、McLachlan, Peter F、Major, John S

  DOI：——

  日期：——
• Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor
  作者：Ursula Tammler、J Mark Quillan、Jochen Lehmann、Wolfgang Sadée、Matthias U Kassack

  DOI：10.1016/s0223-5234(03)00062-x

  日期：2003.5

  Taking the tripeptide D-Trp-Arg-Leu-NH2 as a lead for a Xenopus laevis skin-melanocortin (MC) receptor antagonist, thirteen non-peptidic compounds were synthesized and biologically evaluated at Xenopus laevis melanophores. Six competitive antagonists (shown by Schild analysis) and one partial agonist were identified with moderate activity (IC50: 5-10 muM). Tryptophanamides with aliphatic side chains were inactive whereas basic residues restored activity. Introducing an imidazole residue yielded partial agonist activity (EC50: 32 muM). Interestingly, constraining the inactive S-tryptophan-isoamylamide to a beta-carboline ring yielded an MC receptor antagonist (42). The specificity for MC receptors was tested at various G-protein coupled receptors. In conclusion, the synthesis of non-peptidic MC receptor antagonists is described which may serve as lead compounds for further studies. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.