title: Peptide-small molecule hybrids via orthogonal deprotection-chemoselective conjugation to cysteine-anchored scaffolds. A model study.
abstract: 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]
authors.affiliation: Department of Chemistry and Department of Medicine, School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Savinov
authors.forename: Uma V
authors.initials: UV
authors.lastname: Manjappara
authors.forename: Irwin M
authors.initials: IM
authors.lastname: Chaiken
mesh_terms: D001205:Ascorbic Acid; D003545:Cysteine; D007202:Indicators and Reagents; D010455:Peptides / Q000737:chemistry*; D012663:Semicarbazides
chemical_list: D007202:Indicators and Reagents; D010455:Peptides; D012663:Semicarbazides; C010059:carbamylhydrazine; D003545:Cysteine; D001205:Ascorbic Acid