title: Cysteine-functional polymers via thiol-ene conjugation.
abstract: 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 straightforward approach to cysteine-functional materials.
authors: Department for Functional Materials in Medicine and Dentistry, University of Würzburg, Pleicherwall 2, 97070, Würzburg, Germany.
authors: Matthias
authors: M
authors: Kuhlmann
authors: Oliver
authors: O
authors: Reimann
authors: Christian P R
authors: CP
authors: Hackenberger
authors: Jürgen
authors: J
authors: Groll
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry*; D010084:Oxidation-Reduction; D010446:Peptide Fragments / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013499:Surface Properties; D014302:Trinitrobenzenesulfonic Acid / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D010446:Peptide Fragments; D011108:Polymers; D011409:Propylene Glycols; D013438:Sulfhydryl Compounds; C502907:polyglycidol; D014302:Trinitrobenzenesulfonic Acid; D003545:Cysteine
keywords: chemoselectivity; conjugated polymers; functionalization of polymers; protecting groups; thiol-ene chemistry