Issue 13, 2014

Squaric acid mediated bioconjugation expanded to polymers prepared by ATRP

Abstract

The squaric acid mediated bioconjugation reaction is an attractive approach for the amine-selective protein modification with side-chain functional polymers. This manuscript presents 3 squaric acid based atom transfer radical polymerization (ATRP) initiators that significantly expand the scope of this bioconjugation reaction to a broad range of synthetic polymers that can be prepared by ATRP. Two proof-of-principle studies are discussed that demonstrate the feasibility of these novel initiators for the preparation of protein–synthetic polymer conjugates via both the grafting-onto as well as the grafting-from strategy. ATRP of polyethylene glycol methacrylate (PEGMA) with these initiators was used to generate a library of linear, mid-functional and 3-arm squaric acid functionalized PPEGMA derivatives. These PPEGMA polymers could subsequently be grafted onto bovine serum albumin (BSA), which was selected as a model protein. Alternatively, BSA could also be modified with these squaric acid based initiators to afford protein macroinitiators, which were successfully used to mediate ATRP of PEGMA and generate BSA–PPEGMA conjugates in a grafting-from process.

Graphical abstract: Squaric acid mediated bioconjugation expanded to polymers prepared by ATRP

Supplementary files

Article information

Article type
Paper
Submitted
05 Feb 2014
Accepted
06 Mar 2014
First published
07 Mar 2014

Polym. Chem., 2014,5, 4039-4047

Squaric acid mediated bioconjugation expanded to polymers prepared by ATRP

T. Steinbach, F. Wurm and H. Klok, Polym. Chem., 2014, 5, 4039 DOI: 10.1039/C4PY00168K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements