Peptide-small molecule hybrids via orthogonal deprotection-chemoselective conjugation to cysteine-anchored scaffolds. A model study.
The feasibility of an orthogonal deprotection-conjugation protocol, holding the promise of libraries of functionally diverse chemical probes attached to cysteine-anchored peptide scaffolds, has been explored with a model system. The necessary tools for assembly of the hybrid libraries have been prepared and the tandem procedure optimized. S-alkylation and S-sulfenylation are featured as the chemoselective ligation reactions. [reaction: see text]
Smith
Amos B
AB
Department of Chemistry and Department of Medicine, School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Savinov
Sergey N
SN
Manjappara
Uma V
UV
Chaiken
Irwin M
IM
D001205:Ascorbic Acid; D003545:Cysteine; D007202:Indicators and Reagents; D010455:Peptides / Q000737:chemistry*; D012663:Semicarbazides
D007202:Indicators and Reagents; D010455:Peptides; D012663:Semicarbazides; C010059:carbamylhydrazine; D003545:Cysteine; D001205:Ascorbic Acid