Solid-Phase Synthesis of Peptide Vinyl Sulfones as Potential Inhibitors and Activity-Based Probes of Cysteine Proteases
- 12 February 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (5), 737-740
- https://doi.org/10.1021/ol0275567
Abstract
Peptide vinyl sulfones were prepared from 2-chlorotrityl resin-bound phenolic amino vinyl sulfones in high yield and purity. This method enables the convenient synthesis of peptide vinyl sulfones having different amino acids at the P1 position. It also allows efficient synthesis of vinyl sulfone-containing, activity-based probes of cysteine proteases used in a proteomic experiment.Keywords
This publication has 10 references indexed in Scilit:
- Recent advances in the synthesis, design and selection of cysteine protease inhibitorsCurrent Opinion in Chemical Biology, 2002
- Probing Structural Determinants Distal to the Site of Hydrolysis that Control Substrate Specificity of the 20S ProteasomeChemistry & Biology, 2002
- Extended peptide-based inhibitors efficiently target the proteasome and reveal overlapping specificities of the catalytic β-subunitsChemistry & Biology, 2001
- Global analysis of proteasomal substrate specificity using positional-scanning libraries of covalent inhibitorsProceedings of the National Academy of Sciences, 2001
- Solid phase synthesis of peptide vinyl sulfone and peptide epoxyketone proteasome inhibitorsTetrahedron Letters, 2000
- Substrate binding and sequence preference of the proteasome revealed by active-site-directed affinity probesChemistry & Biology, 1998
- Covalent modification of the active site threonine of proteasomal β subunits and theEscherichia colihomolog HslV by a new class of inhibitorsProceedings of the National Academy of Sciences, 1997
- Solid support linker strategiesCurrent Opinion in Chemical Biology, 1997
- Configurational stability of N-protected .alpha.-amino aldehydesJournal of the American Chemical Society, 1987
- Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninalThe Journal of Organic Chemistry, 1976