Chemo-enzymatic synthesis of polyhydroxyazepanes

✍ Scribed by Peter R. Andreana; Tom Sanders; Adam Janczuk; Joshua I. Warrick; Peng George Wang

• Book ID: 104251799
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 89 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01465-x

✦ Synopsis

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).