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Issue 47, 2016
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Squaric ester amides as hydrolysis-resistant functional groups for protein-conjugation of RAFT-derived polymers

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Abstract

We report on the synthesis of amine-reactive polymers, for the purpose of protein conjugation. Poly(N,N-dimethylacrylamide) (polyDMA) was prepared by RAFT polymerization using either a squaric ester amide functionalized chain transfer agent (CTA) or a phthalimide functionalized CTA which served as a precursor for post-polymerization introduction of a squaric ester amide moiety. Polymers were characterized for their end group fidelity by 1H-NMR and MALDI-TOF MS, which showed the use of a squaric ester amide functionalized CTA to be superior. The performance of these polymers for lysine-targeted protein modification was assessed using lysozyme as model protein and compared to N-hydroxysuccinimide (NHS)-functionalized polymers as the golden standard in bio-conjugation. We found that squaric ester amides were much less prone to hydrolysis, which yielded higher protein-conjugation efficiency in aqueous medium.

Graphical abstract: Squaric ester amides as hydrolysis-resistant functional groups for protein-conjugation of RAFT-derived polymers

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Supplementary files

Article information


Submitted
18 Aug 2016
Accepted
03 Nov 2016
First published
04 Nov 2016

Polym. Chem., 2016,7, 7242-7248
Article type
Paper

Squaric ester amides as hydrolysis-resistant functional groups for protein-conjugation of RAFT-derived polymers

Z. Zhang, N. Vanparijs, S. Vandewalle, F. E. Du Prez, L. Nuhn and B. G. De Geest, Polym. Chem., 2016, 7, 7242
DOI: 10.1039/C6PY01438K

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