Cysteine-Functional Polymers via Thiol-ene Conjugation

被引：17
作者：
Kuhlmann, Matthias [1 ]
Reimann, Oliver [2 ]
Hackenberger, Christian P. R. [2 ,3 ]
Groll, Juergen [1 ]
机构：
[1] Univ Wurzburg, Dept Funct Mat Med & Dent, D-97070 Wurzburg, Germany
[2] Leibniz Inst Mol Pharmakol FMP, Dept Chem Biol 2, D-13125 Berlin, Germany
[3] Humboldt Univ, Dept Chem, D-12489 Berlin, Germany
来源：
MACROMOLECULAR RAPID COMMUNICATIONS | 2015年 / 36卷 / 05期
基金：
欧洲研究理事会;
关键词：
chemoselectivity; conjugated polymers; functionalization of polymers; protecting groups; thiol-ene chemistry; NATIVE CHEMICAL LIGATION; POLYGLYCIDOL; CHEMISTRY; PEPTIDES; PROTEINS;
D O I：
10.1002/marc.201400703
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 ; 080501 ; 081704 ;
摘要：
A thiofunctional thiazolidine is introduced as a new low-molar-mass building block for the introduction of cysteine residues via a thiol-ene reaction. Allyl-functional polyglycidol (PG) is used as a model polymer to demonstrate polymer-analogue functionalization through reaction with the unsaturated side-chains. A modified trinitrobenzenesulfonic acid (TNBSA) assay is used for the redox-insensitive quantification and a precise final cysteine content can be predetermined at the polymerization stage. Native chemical ligation at cysteine-functional PG is performed as a model reaction for a chemoselective peptide modification of this polymer. The three-step synthesis of the thiofunctional thiazolidine reactant, together with the standard thiol-ene coupling and the robust quantification assay, broadens the toolbox for thiol-ene chemistry and offers a generic and straight-forward approach to cysteine-functional materials.
引用
收藏
页码：472 / 476
页数：5
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