Direct on-resin synthesis of peptide-alphathiophenylesters for use in native chemical ligation.
[reaction: see text] A peptide-(alpha)thiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-(alpha)thiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-(alpha)thiophenylesters using a simple and efficient method. The peptide-(alpha)thiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-(alpha)thioalkylester.
Bang
Duhee
D
Institute for Biophysical Dynamics, Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, USA.
Pentelute
Brad L
BL
Gates
Zachary P
ZP
Kent
Stephen B
SB
D000595:Amino Acid Sequence; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics
D001555:Benzene Derivatives; D004952:Esters; D010455:Peptides