title: Aziridine-mediated ligation and site-specific modification of unprotected peptides.
abstract: A synthesis of aziridine-containing peptides via the Cu(II)-promoted coupling of unprotected peptide thioacids and N-H aziridine-2-carbonyl peptides is reported. The unique reactivity of the resulting N-acylated aziridine-2-carbonyl peptides facilitates their subsequent regioselective and stereoselective nucleophilic ring-opening to give unprotected peptides that are specifically modified at the ligation site. The aziridine-mediated peptide ligation concept is exemplified using H(2)O as the nucleophile, producing a Xaa-Thr linkage (where Xaa can be an epimerizable and hindered amino acid). The overall process is compatible with a variety of unprotected amino acid functionality, most notably the N-terminal and Lys side chain amines.
authors: Department of Chemistry, Washington State University, Pullman, Washington 99164-4630, USA.
authors: Frank Brock
authors: FB
authors: Dyer
authors: Chung-Min
authors: CM
authors: Park
authors: Ryan
authors: R
authors: Joseph
authors: Philip
authors: P
authors: Garner
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*
chemical_list: D001388:Aziridines; D010455:Peptides; C033132:aziridine