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Intrastrand foldamer crosslinking by reductive amination Part A Polymer chemistry
- Smaldone, Ronald A., Lin, En-chi, Moore, Jeffrey S.
- Journal of polymer science 2010 v.48 no.4 pp. 927-935
- crosslinking, denaturation, gel chromatography, mass spectrometry, nuclear magnetic resonance spectroscopy, polymers, solvents
- A series of m-phenylene ethynylene (mPE) foldamers were crosslinked in their helical conformation using a reductive amination-based strategy. This was accomplished by placing aldehyde moieties in the backbone of the oligomer at specific residues, which allowed a diamine crosslinker to covalently link the helical loops together. Three different foldamers with crosslinks placed at different locations in the backbone were synthesized and characterized by mass spectrometry, ¹H NMR, and gel permeation chromatography. The effect of the crosslinking on the stability of the folded state was evaluated through solvent denaturation studies. These studies show a reduction in the oligomer's ability to unfold of up to 30% relative to an unmodified mPE oligomer of the same length in solvents that promote unfolding.