Combining RAFT and Staudinger Ligation: A Potentially New Synthetic Tool for Bioconjugate Formation
| Autor: | Sven Fleischmann, Brigitte Voit, Hartmut Komber, Christian Tock, Robert Pötzsch |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Bioconjugation
Polymers and Plastics Organic Chemistry Radical polymerization Chain transfer Inorganic Chemistry chemistry.chemical_compound End-group Polymerization chemistry Polymer chemistry Materials Chemistry Reversible addition−fragmentation chain-transfer polymerization Staudinger reaction Azide |
| Zdroj: | Macromolecules. 44:3260-3269 |
| ISSN: | 1520-5835 0024-9297 |
| DOI: | 10.1021/ma2000724 |
| Popis: | We report a new route for biocompatible polymer end-group modification by means of the Staudinger ligation. This reaction allows the formation of a peptide bond in aqueous media between a phosphine-containing ester functionality and an azide group. Esterification of the two carboxylic acid-containing chain transfer agents (CTAs), 2-(dodecylsulfanylthiocarbonylsulfanyl)-2-methylpropionic acid (1) and 4-cyano-4-(dodecylsulfanylthiocarbonylsulfanyl)pentanoic acid (2), with different appropriate phosphines gave phosphine-containing CTAs. They allowed us to synthesize polystyrene of medium molecular weight via “reversible addition−fragmentation chain transfer” (RAFT) polymerization. 3,6,9-Trioxodecyl azide (TOD-N3) was then used as model compound to study the Staudinger ligation with the corresponding polymers. Among all CTAs tested, the phosphine-functionalized CTA-4, prepared from 2 and P-borane-(diphenylphosphanyl)methanethiol (6), not only proved to be suitable for RAFT polymerization of styrene but the po... |
| Databáze: | OpenAIRE |
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