N-(tert-butoxycarbonyl)-L-valyl-N1-[(1S,2S)-1-(azidomethyl)-2-methylbutyl]-N2-(4-methoxybenzyl)-2-methylalaninamide | 1316672-47-5

• 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)-L-valyl-N1-[(1S,2S)-1-(azidomethyl)-2-methylbutyl]-N2-(4-methoxybenzyl)-2-methylalaninamide
• 英文别名: tert-butyl N-[(2S)-1-[[1-[[(2S,3S)-1-azido-3-methylpentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]-[(4-methoxyphenyl)methyl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 1316672-47-5
• 化学式: C₂₈H₄₆N₆O₅
• 分子量: 546.71
• InChiKey: QPXIODHMZXINAJ-PMOQBDJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-L-valyl-N1-[(1S,2S)-1-(azidomethyl)-2-methylbutyl]-N2-(4-methoxybenzyl)-2-methylalaninamide 、 美雌醇 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 以70%的产率得到N-(tert-butoxycarbonyl)-L-valyl-N(1)-[(1S,2S)-1-({4-[17-hydroxy-3-methoxyestra-1(10),2,4-trien-17-yl]-1H-1,2,3-triazol-1-yl}methyl)-2-methylbutyl]-N(2)-(4-methoxybenzyl)-2-methylalaninamide
  参考文献：
  名称：

  Synthesis of peptide conjugates of mestranol by a 1,3-dipolar cycloaddition click reaction

  摘要：

  An efficient method is presented for the synthesis of a series of peptide conjugates of the ethynylestradiol 3-methyl ether and the corresponding azidopeptides by a copper(I)-catalyzed 1,3-di-polar cycloaddition click reaction.

  DOI：

  10.1007/s10593-012-1074-3
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 、 (2S,3S)-1-azido-2-isocyano-3-methylpentane 、 4-甲氧基苄胺 、 丙酮 以 甲醇 为溶剂， 反应 24.0h， 以50%的产率得到N-(tert-butoxycarbonyl)-L-valyl-N1-[(1S,2S)-1-(azidomethyl)-2-methylbutyl]-N2-(4-methoxybenzyl)-2-methylalaninamide
  参考文献：
  名称：

  Design and synthesis of bile acid–peptide conjugates linked via triazole moiety

  摘要：

  通过 Cu（I）催化的点击化学，描述了胆汁酸与肽的共轭。利用 Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click "反应)，合成了基于胆酸、去氧胆酸和石胆酸衍生物的通过 1,2,3- 三唑分子连接的新型胆酸肽共轭物。研究表明，多达三个肽片段可以连接到一个中央甾体核心，从而形成复杂的三维多共轭结构，在生物化学、药物化学和配位化学中具有重要的应用价值。

  DOI：

  10.1039/c0ob01188f

文献信息

• Synthesis of α-Trifluoromethyl-α-hydroxy Acid-Peptide Conjugates via Click Chemistry
  作者：Sergey Osipov、Valentine Nenajdenko、Nadezhda Sokolova、Daria Vorobyeva、Tamara Vasilyeva

  DOI：10.1055/s-0031-1289609

  日期：2012.1

  A simple and convenient method for the incorporation of fluorinated α-hydroxy acids into peptides is described. The target conjugates were obtained from α-alkynyl-α-trifluoromethyl-α-hydroxy acids and azido peptides via the copper(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). After straightforward deprotection, the α-trifluoromethyl-α-hydroxy acid containing peptides may find important applications in biochemistry and medicinal chemistry.

  描述了一种简单且便利的方法，将氟化的α-羟基酸引入肽中。目标结合物是通过铜(I)催化的Huisgen环加成反应（点击化学）从α-炔基-α-三氟甲基-α-羟基酸和叠氮肽中获得的。经过简单去保护后，含有α-三氟甲基-α-羟基酸的肽可能在生物化学和药物化学中找到重要应用。
• Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence
  作者：Daria V. Vorobyeva、Nadezhda V. Sokolova、Valentine G. Nenajdenko、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1016/j.tet.2011.11.037

  日期：2012.1

  A convenient synthetic pathway to novel functionalized tetrapeptides containing the 1,2,3-triazole moiety is described. The target molecules were obtained by the reaction of fluorinated alpha-amino acids or alpha-aminophosphonates with azidopeptides via Cu(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). The synthesized tetrapeptides may find important applications in biomedical chemistry as potential drugs. (C) 2011 Elsevier Ltd. All rights reserved.
• Design and synthesis of bile acid–peptide conjugates linked via triazole moiety
  作者：Nadezhda V. Sokolova、Gennadij V. Latyshev、Nikolay V. Lukashev、Valentine G. Nenajdenko

  DOI：10.1039/c0ob01188f

  日期：——

  A conjugation of bile acids with peptidesviaCu(I)-catalyzed click chemistry has been described. Novel bile acid–peptide conjugates linked via a 1,2,3-triazole moiety based on cholic, deoxycholic and lithocholic acid derivatives were synthesized using Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click” reaction). It was shown that up to three peptide fragments can be attached to a central steroid core, thus forming complex three-dimensional polyconjugate structures, which can find important applications in biochemistry, medicinal chemistry, and coordination chemistry.

  通过 Cu（I）催化的点击化学，描述了胆汁酸与肽的共轭。利用 Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click "反应)，合成了基于胆酸、去氧胆酸和石胆酸衍生物的通过 1,2,3- 三唑分子连接的新型胆酸肽共轭物。研究表明，多达三个肽片段可以连接到一个中央甾体核心，从而形成复杂的三维多共轭结构，在生物化学、药物化学和配位化学中具有重要的应用价值。
• Synthesis of peptide conjugates of mestranol by a 1,3-dipolar cycloaddition click reaction
  作者：N. V. Sokolova、V. G. Nenajdenko

  DOI：10.1007/s10593-012-1074-3

  日期：2012.9

  An efficient method is presented for the synthesis of a series of peptide conjugates of the ethynylestradiol 3-methyl ether and the corresponding azidopeptides by a copper(I)-catalyzed 1,3-di-polar cycloaddition click reaction.