title: Building functionalized peptidomimetics: use of electroauxiliaries for introducing N-acyliminium ions into peptides.
abstract: A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.
authors.affiliation: Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
authors.forename: Haizhou
authors.initials: H
authors.lastname: Sun
authors.forename: Connor
authors.initials: C
authors.lastname: Martin
authors.forename: David
authors.initials: D
authors.lastname: Kesselring
authors.forename: Rebecca
authors.initials: R
authors.lastname: Keller
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Moeller
mesh_terms: D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry; D004572:Electrolysis; D007097:Imines / Q000737:chemistry*; D007477:Ions; D008956:Models, Chemical; D018716:Molecular Mimicry; D017646:Organosilicon Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004151:Dipeptides; D007097:Imines; D007477:Ions; D017646:Organosilicon Compounds; D010455:Peptides; D012825:Silicon