Aziridine-2-carboxylic acid-containing peptides: application to solution- and solid-phase convergent site-selective peptide modification.
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.
Galonić
Danica P
DP
Department of Chemistry, University of Illinois, Urbana, 61801, USA.
Ide
Nathan D
ND
van der Donk
Wilfred A
WA
Gin
David Y
DY
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
D001388:Aziridines; D006020:Glycopeptides; D010455:Peptides; D013438:Sulfhydryl Compounds; C073440:aziridine-2-carboxylic acid