title: Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif.
abstract: A synthesis of two (S)-phenylalanine derivatives is described which have the all-cis, 2,3,5,6-tetrafluorocyclohexyl motif attached to the aromatic ring at the meta and para positions; the para substituted isomer is elaborated into illustrative dipeptides via the free amine and carboxylate respectively demonstrating its utility as a novel amino acid for peptide synthesis and offering a vehicle for incorporation of this unique and facially polarized ring system into bioactive compounds.
authors.affiliation: School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. do1@st-andrews.ac.uk.
authors.forename: Mohammed Salah
authors.initials: MS
authors.lastname: Ayoup
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis*; D005461:Fluorine / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D010446:Peptide Fragments / Q000138:chemical synthesis*; D010649:Phenylalanine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004151:Dipeptides; D006571:Heterocyclic Compounds; D010446:Peptide Fragments; D005461:Fluorine; D010649:Phenylalanine