Squaric ester amides as hydrolysis-resistant functional groups for protein-conjugation of RAFT-derived polymers
Literature Information
Publication Date
2016-11-04
DOI
10.1039/C6PY01438K
Impact Factor
5.582
Authors
Zhiyue Zhang, Nane Vanparijs, Stef Vandewalle, Filip E. Du Prez, Lutz Nuhn, Bruno G. De Geest
View Original
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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Source Journal
Polymer Chemistry
CiteScore:
8.6
Self-citation Rate:
7.3%
Articles per Year:
457
Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.
Recommended Compounds
5-(2-Methyl-3-furyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
CAS Number:
346464-59-3
Molecular Formula:
C13H11N3OS
![(1R,5R)-3-{[(2-Methyl-2-propanyl)oxy]carbonyl}-3-azabicyclo[3.1.0]hexane-1-carboxylic acid structure](https://static.chemtradehub.com/structs/116/1165450-63-4-bfe1.webp "(1R,5R)-3-{[(2-Methyl-2-propanyl)oxy]carbonyl}-3-azabicyclo[3.1.0]hexane-1-carboxylic acid structure")
(1R,5R)-3-{[(2-Methyl-2-propanyl)oxy]carbonyl}-3-azabicyclo[3.1.0]hexane-1-carboxylic acid
CAS Number:
1165450-63-4
Molecular Formula:
C11H17NO4
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