title: Aziridine-2-carboxylic acid-containing peptides: application to solution- and solid-phase convergent site-selective peptide modification.
abstract: The development of a method for site- and stereoselective peptide modification using aziridine-2-carboxylic acid-containing peptides is described. A solid-phase peptide synthesis methodology that allows for the rapid generation of peptides incorporating the aziridine residue has been developed. The unique electrophilic nature of this nonproteinogenic amino acid allows for site-selective conjugation with various thiol nucleophiles, such as anomeric carbohydrate thiols, farnesyl thiol, and biochemical tags, both in solution and on solid support. This strategy, combined with native chemical ligation, provides convergent and rapid access to complex thioglycoconjugates.
authors.affiliation: Department of Chemistry, University of Illinois, Urbana, 61801, USA.
authors.forename: Danica P
authors.initials: DP
authors.lastname: Galonić
authors.forename: Nathan D
authors.initials: ND
authors.lastname: Ide
authors.forename: Wilfred A
authors.initials: WA
authors.lastname: van der Donk
authors.forename: David Y
authors.initials: DY
authors.lastname: Gin
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001388:Aziridines; D006020:Glycopeptides; D010455:Peptides; D013438:Sulfhydryl Compounds; C073440:aziridine-2-carboxylic acid