Site-selective conjugation of thiols with aziridine-2-carboxylic acid-containing peptides.
The synthesis and convergent site-selective conjugation of aziridine-2-carboxylic acid-containing peptides with thiols, both in solution and on solid support, are described. The synthesis and use of FmocAzyOH in this capacity demonstrate both the efficient incorporation and tolerance of the Azy moiety in multistep Fmoc solid-phase peptide synthesis (SPPS), as well as the competence of solution and on-bead ligation through a highly regioselective base-promoted aziridine ring-opening process.
Galonić
Danica P
DP
Department of Chemistry, University of Illinois, Urbana, IL 61801, USA.
van der Donk
Wilfred A
WA
Gin
David Y
DY
D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D001388:Aziridines; D009842:Oligopeptides; D013438:Sulfhydryl Compounds; C073440:aziridine-2-carboxylic acid