Syntheses of Atypically Fluorinated Peptidyl Macrocycles through Sequential Vinylic Substitutions.

Tomoyuki Tsunemi, Salvador J Bernardino, Angel Mendoza, Christopher G Jones, Patrick G Harran

Angewandte Chemie (International ed. in English) 2020 Jan 07

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Small peptides containing combinations of cysteine, tyrosine, histidine, and serine residues react with octafluorocyclopentene (OFCP) to afford atypically structured macrocycles through successive vinylic substitutions. The reactions proceed rapidly in air at 0 °C and are tolerant of spectating tryptophan, asparagine, glutamine, and threonine residues. Hexapeptides of consensus sequence YXCXXC displace four fluorine atoms from OFCP to generate fluorinated macrobicyclic compounds that display dual-turn surfaces. The method provides facile access to a wide range of previously unknown heterocyclic structures. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Tomoyuki Tsunemi, Salvador J Bernardino, Angel Mendoza, Christopher G Jones, Patrick G Harran. Syntheses of Atypically Fluorinated Peptidyl Macrocycles through Sequential Vinylic Substitutions. Angewandte Chemie (International ed. in English). 2020 Jan 07;59(2):674-678