Solid-phase synthesis of peptide vinyl sulfones as potential inhibitors and activity-based probes of cysteine proteases.
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 P(1) position. It also allows efficient synthesis of vinyl sulfone-containing, activity-based probes of cysteine proteases used in a proteomic experiment.
Wang
Gang
G
Departments of Chemistry and Biological Sciences, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore.
Mahesh
Uttamchandani
U
Chen
Grace Y J
GY
Yao
Shao Q
SQ
D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D003546:Cysteine Endopeptidases / Q000378:metabolism*; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D015335:Molecular Probes / Q000138:chemical synthesis; D020543:Proteome / Q000378:metabolism; D013450:Sulfones / Q000138:chemical synthesis* / Q000494:pharmacology; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D000596:Amino Acids; D015853:Cysteine Proteinase Inhibitors; D015335:Molecular Probes; D020543:Proteome; D013450:Sulfones; D014753:Vinyl Compounds; D003546:Cysteine Endopeptidases