New aldehyde‐functional methacrylic water‐soluble polymers

Abstract

Aldehyde groups enable facile conjugation to proteins, enzymes, oligonucleotides or fluorescent dyes, yet there are no literature examples of water‐soluble aldehyde‐functional vinyl monomers. Herein we report the synthesis of a new hydrophilic cis ‐diol‐based methacrylic monomer (GEO5MA) by transesterification of isopropylideneglycerol penta(ethylene glycol) using methyl methacrylate followed by acetone deprotection via acid hydrolysis. The corresponding water‐soluble aldehyde monomer, AGEO5MA, is prepared by aqueous periodate oxidation of GEO5MA at 22 °C. RAFT polymerization of GEO5MA yields the water‐soluble homopolymer, PGEO5MA. Aqueous periodate oxidation of the terminal cis ‐diol units on PGEO5MA at 22 °C affords a water‐soluble aldehyde‐functional homopolymer (PAGEO5MA). Moreover, a library of hydrophilic statistical copolymers bearing cis ‐diol and aldehyde groups is prepared using sub‐stoichiometric periodate/ cis ‐diol molar ratios. The aldehyde groups on PAGEO5MA homopolymer are reacted in turn with three amino acids to exemplify synthetic utility, which is expected to offer new applications in the fields of cell biology and biomaterials.

Metadata

Authors/Creators:

Brotherton, E.E. https://orcid.org/0000-0001-5005-3205
Jesson, C.P.
Warren, N.J.
Smallridge, M.J.
Armes, S.P. https://orcid.org/0000-0002-8289-6351

© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/4.0/) which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Keywords:

aldehyde-functional methacrylic monomer; water-soluble polymers; RAFT polymerization; periodate oxidation; Block copolymers

Dates: