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Peptide-small molecule hybrids via orthogonal deprotection-chemoselective conjugation to cysteine-anchored scaffolds.
Amos B Smith1, Sergey N Savinov, Uma V Manjappara
1Department of Chemistry and Department of Medicine, School of Medicine, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Organic Letters
|November 9, 2002
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]