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Issue 19, 2013
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Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

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Abstract

Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference.

Graphical abstract: Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

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Publication details

The article was received on 06 Mar 2013, accepted on 26 Mar 2013 and first published on 27 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40463C
Citation: Org. Biomol. Chem., 2013,11, 3168-3176
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    Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers

    S. J. Pike, M. De Poli, W. Zawodny, J. Raftery, S. J. Webb and J. Clayden, Org. Biomol. Chem., 2013, 11, 3168
    DOI: 10.1039/C3OB40463C

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