Biosynthesis of the azoxycarboxamide lyophyllin and formation of some of its unnatural analogues in fruit-bodies of Lyophyllum connatum

Abstract The azoxy compound lyophyllin ( 3 ) is formed in fruit-bodies of the toadstool Lyophyllum connatum by oxidative condensation of N -hydroxy- N ′, N ′-dimethylurea ( 2 ) with N -methylhydroxylamine ( 4 ). The condensing enzyme is remarkably unspecific and transforms a variety of hydroxyureas and N -alkyl-hydroxylamines into the corresponding lyophyllin analogues 5 . © 1997 Elsevier Science Ltd.