(4S)-5-[(2S,3S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-[N-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-6-amino-1-hydroxy-1-[(2S,3S)-1-hydroxy-1-[(2S)-1-hydroxy-1-imino-4-methylpentan-2-yl]imino-3-methylpentan-2-yl]iminohexan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]imino-1-hydroxypropan-2-yl]-C-hydroxycarbonimidoyl]pyrrolidin-1-yl]-5-[[N-[2-[2-[4-[[3-[3-[5-hydroxy-4-(1-methylindol-3-yl)-2-oxopyrrol-3-yl]indol-1-yl]propyl-methylamino]methyl]triazol-1-yl]ethoxy]ethyl]carbamimidoyl]amino]-1-oxopentan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1,3-dihydroxypropan-2-yl]imino-1-hydroxy-4-methylpentan-2-yl]imino-1-hydroxy-3-methylpentan-2-yl]imino-5-hydroxy-4-(1-hydroxyethylideneamino)pentanoic acid | 1226853-64-0

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: (4S)-5-[(2S,3S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-[N-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-6-amino-1-hydroxy-1-[(2S,3S)-1-hydroxy-1-[(2S)-1-hydroxy-1-imino-4-methylpentan-2-yl]imino-3-methylpentan-2-yl]iminohexan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]imino-1-hydroxypropan-2-yl]-C-hydroxycarbonimidoyl]pyrrolidin-1-yl]-5-[[N-[2-[2-[4-[[3-[3-[5-hydroxy-4-(1-methylindol-3-yl)-2-oxopyrrol-3-yl]indol-1-yl]propyl-methylamino]methyl]triazol-1-yl]ethoxy]ethyl]carbamimidoyl]amino]-1-oxopentan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1,3-dihydroxypropan-2-yl]imino-1-hydroxy-4-methylpentan-2-yl]imino-1-hydroxy-3-methylpentan-2-yl]imino-5-hydroxy-4-(1-hydroxyethylideneamino)pentanoic acid
• CAS: 1226853-64-0
• 化学式: C₁₀₇H₁₆₃N₃₁O₂₁
• 分子量: 2219.67
• InChiKey: QCUJMAOZSJPAMC-KJVUVCIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  159
• 可旋转键数：
  73
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  787
• 氢给体数：
  27
• 氢受体数：
  28

反应信息

• 作为产物：
  描述：

  3-(1-Methylindol-3-yl)-4-[1-[3-[methyl(prop-2-ynyl)amino]propyl]indol-3-yl]pyrrole-2,5-dione 、 (4S)-4-acetamido-5-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S,3S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-[[amino-[2-(2-azidoethoxy)ethylamino]methylidene]amino]-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.33h， 以62%的产率得到(4S)-5-[(2S,3S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-[N-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-6-amino-1-hydroxy-1-[(2S,3S)-1-hydroxy-1-[(2S)-1-hydroxy-1-imino-4-methylpentan-2-yl]imino-3-methylpentan-2-yl]iminohexan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]imino-1-hydroxypropan-2-yl]-C-hydroxycarbonimidoyl]pyrrolidin-1-yl]-5-[[N-[2-[2-[4-[[3-[3-[5-hydroxy-4-(1-methylindol-3-yl)-2-oxopyrrol-3-yl]indol-1-yl]propyl-methylamino]methyl]triazol-1-yl]ethoxy]ethyl]carbamimidoyl]amino]-1-oxopentan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1,3-dihydroxypropan-2-yl]imino-1-hydroxy-4-methylpentan-2-yl]imino-1-hydroxy-3-methylpentan-2-yl]imino-5-hydroxy-4-(1-hydroxyethylideneamino)pentanoic acid
  参考文献：
  名称：

  Preparation of novel alkylated arginine derivatives suitable for click-cycloaddition chemistry and their incorporation into pseudosubstrate- and bisubstrate-based kinase inhibitors

  摘要：

  本文介绍了在精氨酸残基侧链中引入乙炔或叠氮取代基的有效策略。取代基的引入可保持胍基的碱性。该方法可用于含精氨酸肽的非侵入性标记。通过在蛋白激酶 C (PKC) 伪底物多肽中引入 "点击 "处理，以及随后制备和评估基于这种多肽的新型双底物抑制剂，证明了该方法的适用性。

  DOI：

  10.1039/b922928k

文献信息

• Preparation of novel alkylated arginine derivatives suitable for click-cycloaddition chemistry and their incorporation into pseudosubstrate- and bisubstrate-based kinase inhibitors
  作者：Jeroen van Ameijde、Alex J. Poot、Loek T. M. van Wandelen、Angelique E. M. Wammes、Rob Ruijtenbeek、Dirk T. S. Rijkers、Rob M. J. Liskamp

  DOI：10.1039/b922928k

  日期：——

  Efficient strategies for the introduction of arginine residues featuring acetylene or azide moieties in their side chains are described. The substituents are introduced in a way that maintains the basicity of the guanidine moiety. The methodology can be used e.g. for non-invasive labeling of arginine-containing peptides. Its applicability is demonstrated by the introduction of ‘click’ handles into a Protein Kinase C (PKC) pseudosubstrate peptide, and the subsequent preparation and evaluation of a novel bisubstrate-based inhibitor based on such a peptide.

  本文介绍了在精氨酸残基侧链中引入乙炔或叠氮取代基的有效策略。取代基的引入可保持胍基的碱性。该方法可用于含精氨酸肽的非侵入性标记。通过在蛋白激酶 C (PKC) 伪底物多肽中引入 "点击 "处理，以及随后制备和评估基于这种多肽的新型双底物抑制剂，证明了该方法的适用性。