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

Zhang, Z., Vanparijs, N., Vandewalle, S., Du Prez, F. E., Nuhn, L., & De Geest, B. G. (2016). Squaric ester amides as hydrolysis-resistant functional groups for protein-conjugation of RAFT-derived polymers. Polymer Chemistry, 7(47), 7242-7248. doi:10.1039/C6PY01438K.

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 Creators:
Zhang, Zhiyue, Author
Vanparijs, Nane, Author
Vandewalle, Stef, Author
Du Prez, Filip E., Author
Nuhn, Lutz1, Author           
De Geest, Bruno G., Author
Affiliations:
1Univ Ghent, Dept Pharmaceut, Ghent, Belgium, ou_persistent22              

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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.

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Language(s): eng - English
 Dates: 2016
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1039/C6PY01438K
BibTex Citekey: C6PY01438K
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Title: Polymer Chemistry
  Abbreviation : Polym. Chem.
Source Genre: Journal
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Publ. Info: Cambridge, UK : Royal Society of Chemistry
Pages: - Volume / Issue: 7 (47) Sequence Number: - Start / End Page: 7242 - 7248 Identifier: ISSN: 1759-9954
CoNE: https://pure.mpg.de/cone/journals/resource/1759-9954