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Authors
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Pötzsch, R. ; Fleischmann, S. ; Tock, C. ; Komber, H. ; Voit, B.
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Title
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Combining RAFT and Staudinger ligation: a potentially new synthetic tool for bioconjugate formation
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Date
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28.04.2011
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Number
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27166
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Abstract
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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 polymer-bound P-borane-(diphenylphosphanyl)methyl thioester group also showed the best performance in the subsequent polymer analogous Staudinger ligation.
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Publisher
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Macromolecules
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Wikidata
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Q57777429
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Citation
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Macromolecules 44 (2011) 3260-3269
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DOI
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https://doi.org/10.1021/MA2000724
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Tags
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transfer radical polymerization click-chemistry block-copolymers functional polymers versatile method conjugation azide cycloaddition peptide science
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