title: Aziridine electrophiles in the functionalisation of peptide chains with amine nucleophiles.
abstract: We describe herein the synthesis of aziridine-containing amino acids embedded within tripeptide structures. A range of amine nucleophiles have been shown to open the aziridine amino acid regioselectively at the β-position under mild conditions and without the requirement for a catalyst, forming new adducts in the process. Amino acid N-termini (or an N-containing sidechain) also served as effective nucleophiles for such aziridines and this concept could be extended to encompass a di- or tripeptide nitrogen as a nucleophile, thus providing new methodology for linking together peptide strands using an amine linker.
authors.affiliation: Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Anatol P
authors.initials: AP
authors.lastname: Spork
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
mesh_terms: D000588:Amines / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001388:Aziridines; D010455:Peptides; C033132:aziridine