Mal-Ala-Lys-Tyr-Gly-NH2; Mal = 3-maleimidopropanoyl | 1432063-01-8

• 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: Mal-Ala-Lys-Tyr-Gly-NH2; Mal = 3-maleimidopropanoyl
• CAS: 1432063-01-8
• 化学式: C₂₇H₃₇N₇O₈
• 分子量: 587.633
• InChiKey: QSKFQWCIHUVRAJ-VDGAXYAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.55
• 重原子数：
  42.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  243.12
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 Mal-Ala-Lys-Tyr-Gly-NH2; Mal = 3-maleimidopropanoyl 在 乙酸–三乙胺 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Protected Maleimide Building Blocks for the Decoration of Peptides, Peptoids, and Peptide Nucleic Acids

  摘要：

  Monomers allowing for the introduction of [2,5-dimethylfuran]-protected maleimides into polyamides such as peptides, peptide nucleic acids, and peptoids were prepared, as well as the corresponding oligomers. Suitable maleimide deprotection conditions were established in each case. The stability of the adducts generated by Michael-type maleimide-thiol reaction and Diels-Alder cycloaddition to maleimide deprotection conditions was exploited to prepare a variety of conjugates from peptide and PNA scaffolds incorporating one free and one protected maleimide. The target molecules were synthesized by using two subsequent maleimide-involving click reactions separated by a maleimide deprotection step. Carrying out maleimide deprotection and conjugation simultaneously gave better results than performing the two reactions subsequently.

  DOI：

  10.1021/bc4000614
• 作为产物：
  描述：

  以 甲苯 为溶剂， 生成 Mal-Ala-Lys-Tyr-Gly-NH2; Mal = 3-maleimidopropanoyl
  参考文献：
  名称：

  Protected Maleimide Building Blocks for the Decoration of Peptides, Peptoids, and Peptide Nucleic Acids

  摘要：

  Monomers allowing for the introduction of [2,5-dimethylfuran]-protected maleimides into polyamides such as peptides, peptide nucleic acids, and peptoids were prepared, as well as the corresponding oligomers. Suitable maleimide deprotection conditions were established in each case. The stability of the adducts generated by Michael-type maleimide-thiol reaction and Diels-Alder cycloaddition to maleimide deprotection conditions was exploited to prepare a variety of conjugates from peptide and PNA scaffolds incorporating one free and one protected maleimide. The target molecules were synthesized by using two subsequent maleimide-involving click reactions separated by a maleimide deprotection step. Carrying out maleimide deprotection and conjugation simultaneously gave better results than performing the two reactions subsequently.

  DOI：

  10.1021/bc4000614

文献信息

• On-Resin Conjugation of Diene–Polyamides and Maleimides via Diels–Alder Cycloaddition
  作者：Omar Brun、Xavier Elduque、Enrique Pedroso、Anna Grandas

  DOI：10.1021/acs.joc.5b00592

  日期：2015.6.19

  The reaction between maleimides and resin-linked diene–polyamides allows the latter to be used in the preparation of conjugates. Conjugation takes place by reacting the insoluble, hydrophobic diene component either with water-soluble dienophiles or with dienophiles requiring mixtures of water and organic solvents. Experimental conditions can be adjusted to furnish the target conjugate in good yield

  马来酰亚胺与树脂连接的二烯-聚酰胺之间的反应使后者可用于制备共轭物。通过使不溶的疏水性二烯组分与水溶性的亲二烯体或需要水和有机溶剂的混合物的亲二烯体反应而发生共轭。可以调节实验条件以高产率提供目标缀合物，而无需添加大量过量的可溶性试剂。如果使用受保护的马来酰亚胺，可以同时进行马来酰亚胺的脱保护和Diels-Alder环加成反应，以使缀合物具有不同的连接位置。与未反应的二烯确实在这些条件下降解的相反，树脂上的共轭反应之后进行的是酸性处理，该处理去除了聚酰胺保护基，而对环加合物无害。