title: Postsynthetic modification of peptides via chemoselective N-alkylation of their side chains.
abstract: A chemoselective, mild, and versatile method for performing postsynthetic modifications of peptide sequences is described. It requires only activated molecular sieves in the presence of an alkyl halide in order to N-alkylate lysine side chains. This reaction is fully compatible with most of the peptide functionalities, discriminates the reactivity of differently protected lysines, and proceeds in good yield. The mild conditions employed were further proved by performing the N-alkylation of a peptide containing a disulfide bridge.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309, USA.
authors.forename: Luca
authors.initials: L
authors.lastname: Monfregola
authors.forename: Marilisa
authors.initials: M
authors.lastname: Leone
authors.forename: Enrica
authors.initials: E
authors.lastname: Calce
authors.forename: Stefania
authors.initials: S
authors.lastname: De Luca
mesh_terms: D000478:Alkylation; D000595:Amino Acid Sequence; D004220:Disulfides / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000737:chemistry*
chemical_list: D004220:Disulfides; D010455:Peptides; D008239:Lysine