Examination of N-hydroxylation as a prerequisite mechanism of nitric oxide synthase inactivation

-N5-(1-Hydroxyiminoethyl)-ornithine ( -NHIO) and -N6-(1-hydroxyiminoethyl)-lysine ( -NHIL) were synthesized and tested as potential intermediates in the mechanism-based inactivation of nitric oxide synthase (NOS) by -N5-iminoethyl-ornithine ( -NIO) and -N6-iminoethyllysine ( -NIL). Although these compounds were determined to be competitive inhibitors, mechanism-based inactivation was not observed.