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Syntheses of Atypically Fluorinated Peptidyl Macrocycles through Sequential Vinylic Substitutions
Author(s) -
Tsunemi Tomoyuki,
Bernardino Salvador J.,
Mendoza Angel,
Jones Christopher G.,
Harran Patrick G.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201910136
Subject(s) - chemistry , asparagine , glutamine , histidine , cysteine , serine , tyrosine , threonine , stereochemistry , sequence (biology) , tryptophan , amino acid , combinatorial chemistry , biochemistry , phosphorylation , enzyme
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.