N^α-tert-butoxycarbonyl-L-alanyl-L-lysyl-L-alanine methyl ester | 155479-34-8

• 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^α-tert-butoxycarbonyl-L-alanyl-L-lysyl-L-alanine methyl ester
• 英文别名: Boc-L-Ala-L-Lys-L-Ala-OMe；Boc-Ala-Lys-Ala-OMe；methyl (2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]hexanoyl]amino]propanoate
• CAS: 155479-34-8
• 化学式: C₁₈H₃₄N₄O₆
• 分子量: 402.491
• InChiKey: PZDVLEIIFDWNPU-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N^α-tert-butoxycarbonyl-L-alanyl-L-lysyl-L-alanine methyl ester 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester
  参考文献：
  名称：

  Design and synthesis of novel peptides bearing a host and a guest side chains

  摘要：

  The synthesis of model heptapeptides bearing a host and a guest side chains at different positions is reported. These peptidic structures were designed in such a way that specific backbone; conformations could be induced and stabilized by cooperative side chain interactions. Although circular dichroism studies demonstrated that intra- and intermolecular host guest interactions are involved in the stabilization of the peptidic conformation, they are not strong enough to induce a complete conformational reorganization.

  DOI：

  10.1016/s0040-4020(01)80813-9
• 作为产物：
  描述：

  BOC-(Z)Lys-Ala-OMe 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 6.0h， 生成 N^α-tert-butoxycarbonyl-L-alanyl-L-lysyl-L-alanine methyl ester
  参考文献：
  名称：

  Design and synthesis of novel peptides bearing a host and a guest side chains

  摘要：

  The synthesis of model heptapeptides bearing a host and a guest side chains at different positions is reported. These peptidic structures were designed in such a way that specific backbone; conformations could be induced and stabilized by cooperative side chain interactions. Although circular dichroism studies demonstrated that intra- and intermolecular host guest interactions are involved in the stabilization of the peptidic conformation, they are not strong enough to induce a complete conformational reorganization.

  DOI：

  10.1016/s0040-4020(01)80813-9

文献信息

• Tailoring Peptide-Nucleotide Conjugates (PNCs) for Nucleotide Delivery in Bacterial Cells
  作者：Swarup De、Elisabetta Groaz、Piet Herdewijn

  DOI：10.1002/ejoc.201301781

  日期：2014.4

  synthesis of peptide-2′-deoxythymidine-5′-O-monophosphate conjugates as potential active delivery systems for nucleotides into auxotrophic E. coli strains is presented. A series of oligopeptides were allowed to react with 5′-O-(dibenzylphosphate)-2′-deoxythymidine or its suitably 3′-derivatized analogues to give the relevant peptide–nucleotide adducts, by the formation of a biolabile chemical connection

  介绍了肽-2'-脱氧胸苷-5'-O-单磷酸结合物的设计和合成，作为核苷酸进入营养缺陷型大肠杆菌菌株的潜在活性传递系统。通过形成生物不稳定的化学连接，允许一系列寡肽与 5'-O-（二苄基磷酸酯）-2'-脱氧胸苷或其适当的 3'-衍生类似物反应，得到相关的肽-核苷酸加合物。使用基于正交保护和激活原理的策略，对接头和肽部分进行了合理的变化，以调整缀合物的代谢稳定性。