Small-molecule inhibitor: syringolin A

Summary Structure Literature

Name

Common name: syringolin A
Other names: isosyringolin A; SylA

Inhibition

Mechanism: The crystal structure of the yeast proteasome in complex with syringolin A revealed the mechanism of binding to the catalytic subunits, in which the alpha,beta-unsaturated amide of syringolin A is attacked by the N-terminal threonine of the catalytic beta-subunits, resulting in an irreversible, covalent ether bond (Groll et al., 2008).

Chemistry

CID at PubChem: 24978526
Structure
Chemical/biochemical name: N-[(1-{[(3E,9Z)-5-isopropyl-2,7-dioxo-1,6-diazacyclododeca-3,9-dien-8-yl]carbamoyl}-2-methylpropyl)carbamoyl]valine
Formula weight: 494
Related inhibitors: Syringolin A belongs to the syrbactin class of compound that includes other syringolins (syringolin B, syringolin C) and gliobactins (Groll et al., 2008).