Chemo-enzymatic synthesis of polyhydroxyazepanes

Galactose oxidase (EC 1.1.3.9, GAO) is an extracellular copper-containing enzyme that utilizes molecular oxygen to convert the C6-primary hydroxyl moiety of d-galactopyranosides to hydrated aldehydes. Subsequent dehydratative coupling with hydroxylamines produces oximes (3a–f), which, when subjected to conditions of hydrogenolysis, give rise to polyhydroxyazepanes (11–17).