The Nitro Group as a Masked Electrophile in Covalent Enzyme Inhibition.

Authors
Category Primary study
JournalACS chemical biology
Year 2018
We report the unprecedented reaction between a nitroalkane and an active-site cysteine residue to yield a thiohydroximate adduct. Structural and kinetic evidence suggests the nitro group is activated by conversion to its nitronic acid tautomer within the active site. The nitro group, therefore, shows promise as a masked electrophile in the design of covalent inhibitors targeting binding pockets with appropriately placed cysteine and general acid residues.
Epistemonikos ID: 694a86003c41e1b2c8a1b1c49116eab17620badc
First added on: Nov 03, 2024