Issue 11, 2018

Synthesis of a deoxyguanosine monophosphate rich propyl methacrylate oligomer

Abstract

We report on the first synthesis of a “protected” 5′-dimethoxytrityl-N-isobutyryl-2′-deoxyguanosine(dG), 3′-[(2-cyanoethyl)-2-(methacryloyloxy)propyl]-monophosphate monomer through a modified phosphoramidite coupling method. Here, 2-hydroxylpropyl methacrylate (HPMA) was coupled to a protected 5′-dimethoxytrityl-N-isobutyryl-2′-deoxyguanosine, 3′-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite. Subsequent reversible addition fragmentation chain transfer (RAFT) polymerisation of the protected monomer, followed by deprotection, produced poly[2-(deoxyguanosine-3′-phospho)propyl methacrylate] (poly(dG-P-PMA)). In situ1H nuclear magnetic resonance spectroscopy showed the polymerisation kinetics were consistent with RAFT with dispersity indices (Đ's) <1.2. Circular dichroism showed that the isolated deprotected deoxyguanosine rich oligomers formed stacked G-quartets in both Li+ and K+ ion solutions. These structures were further investigated with confocal fluorescence microscopy.

Graphical abstract: Synthesis of a deoxyguanosine monophosphate rich propyl methacrylate oligomer

Supplementary files

Article information

Article type
Paper
Submitted
28 Feb 2018
Accepted
16 Apr 2018
First published
18 Apr 2018

New J. Chem., 2018,42, 8815-8822

Author version available

Synthesis of a deoxyguanosine monophosphate rich propyl methacrylate oligomer

M. J. Wilson, R. A. Fenati, E. G. L. Williams and A. V. Ellis, New J. Chem., 2018, 42, 8815 DOI: 10.1039/C8NJ00989A

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