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Application of the rule of shielding in the design of novel fluorinated molecules and peptidomimetics

Dalvit, Claudio and Young Ko, Soo and Vulpetti, Anna (2013) Application of the rule of shielding in the design of novel fluorinated molecules and peptidomimetics. Journal of Fluorine Chemistry, 152. pp. 129-135. ISSN 0022-1139

Abstract

The local environment around the fluorine, which determines the 19F chemical shift, appears to be of paramount importance for the recognition mechanism. Deshielded fluorinated fragments, suitable for interacting efficiently with the amphiphatic α helix secondary structural motif, are discussed. Shielded fluorinated scaffolds are proposed as novel peptide bond isosteres for potentially overcoming the major drawbacks of peptides, such as short physiological half-lives due to rapid proteolysis and poor bioavailability. These new fluorinated skeletons can be used for generating a diverse library of fluorinated peptide mimetics which can then be effectively screened in mixtures against multiple targets by 19F NMR spectroscopy.

Item Type: Article
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Additional Information: This manuscript will be part of a special issue of Journal of Fluorine Chemistry with invited contributions by the speakers at the "Fluorine Day" meeting, which took place in Valencia, 20-24 May, 2012 (speaker: C.Dalvit). The chemical motifs shown in the manuscript have been already disclosed by C.Dalvit.
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Date Deposited: 13 Oct 2015 13:13
Last Modified: 13 Oct 2015 13:13
URI: https://oak.novartis.com/id/eprint/9022

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