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Pröhl, Michael ; Englert, Christoph ; Gottschaldt, Michael ; Brendel, Johannes C. ; Schubert, Ulrich S.:
RAFT polymerization and thio‐bromo substitution : An efficient way towards well‐defined glycopolymers.
In: Journal of Polymer Science Part A: Polymer Chemistry.
Bd. 55
(2017)
Heft 21
.
- S. 3617-3626.
ISSN 0360-6376
DOI: https://doi.org/10.1002/pola.28745
Abstract
Despite an increasing effort to design well-defined glycopolymers, the convenient synthesis of polymers with higher DPs (>100) and without tedious protection and deprotection steps remains a challenge. Combining the reversible addition fragmentation transfer (RAFT) polymerization and the efficient substitution of primary bromo groups by thiols, we were able to synthesize a set of well-defined glycopolymers with DPs of up to 115. With the polymerization of the highly reactive monomer (2-bromoethyl)-acrylate polymers with low dispersities were obtained that could efficiently be functionalized with various sugar thiol(ate)s. In particular, derivatives of d-glucose, d-galactose, and d-mannose gave excellent degrees of functionalization close to quantitative conversion using only a slight excess of the thiol. This atom efficient synthesis can even be applied for copolymers with acid or base labile components due to the use of unprotected sugar moieties and, hence, the lack of further deprotection steps. Binding studies with the lectin concanavalin A and the subsequent competition studies with α-d-methyl-mannopyranose (αMeMan) proved the effective binding of these derivatives and revealed a DP- and carbohydrate-dependent clustering and dissolution.
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| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Institutionen der Universität: | Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Makromolekulare Chemie I Fakultäten Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Makromolekulare Chemie I > Lehrstuhl Makromolekulare Chemie I - Univ.-Prof. Dr. Johannes C. Brendel |
| Titel an der UBT entstanden: | Nein |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 19 Feb 2024 12:51 |
| Letzte Änderung: | 02 Mai 2024 07:39 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/88607 |