Structural and enzyme activity studies demonstrate that aryl substituted 2,3-butadienamine analogs inactivate Arthrobacter globiformis amine oxidase (AGAO) by chemical derivatization of the 2,4,5-trihydroxyphenylalanine quinone (TPQ) cofactor

► 5-phenoxy-2,3-pentadienylamine inactivates Arthrobacter globiformis amine oxidase (AGAO). ► 6-phenyl-2,3-hexadienylamine inactivates AGAO. ► Crystal structures of AGAO attached to inactivators reveal mechanism of action. ► IC50 values reveal inhibition potency and suggest selectivity in AGAO inactivation. ►Structural framework to guide the design of selective mechanism-based inhibitors.