Convergent access to mono-fluoroalkene-based peptidomimetics.

The convergent and selective preparation of (Z)-monofluoroalkene-based dipeptide isosteres from functionalized fluorosulfones as a cornerstone is described. In this approach, the N-terminal amino group is introduced by a conjugate addition reaction of phthalimide onto fluorinated vinylsulfones containing α-amino-acid side chains while the C-terminal motif is linked to the fluorovinylic peptide bond mimic via the Julia-Kocienski reaction between fluorosulfones and substituted aldehydes bearing α-amino-acid side chains.

Citation

Florent Larnaud, Charlène Calata, Anaïs Prunier, Clothilde Le Guen, Rémi Legay, Emmanuel Pfund, Thierry Lequeux. Convergent access to mono-fluoroalkene-based peptidomimetics. Organic & biomolecular chemistry. 2022 Feb 09;20(6):1205-1218

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PMID: 35075471

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