Journal
ACS CHEMICAL BIOLOGY
Volume 13, Issue 6, Pages 1470-1473Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acschembio.8b00225
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Funding
- NSF CAREER Award [CHE1255136]
- NIH [GM-116957]
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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.
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