Preparation of iminosugars from aminopolyolsviaselective oxidation using galactose oxidase

Abstract

Minimally protected aminopolyols are novel substrates for the galactose oxidase variant F2. Site-selective oxidation proceeds at the terminal primary alcohol, followed by spontaneous cyclisation to afford stable hemiaminal/hemiacetal anomers of...

Enzyme‐Triggered Reactions for the Synthesis of Organic Molecules

“…This work was followed up by Yeow et al . who accessed the primary oxidation products 21 from aminopolyols 22 , by employing the galactose oxidase F 2 variant (GOase F 2 ) to trigger the cyclisation (Scheme 4c) [12] . The N ‐Cbz protected hemiaminal cyclic products 15 , 20 , and 21 (Scheme 4a‐c) are all stable compounds that were often isolated as a mixture of hemiaminal and hemiacetal anomers.…”

“…This work was followed up by Yeow et al who accessed the primary oxidation products 21 from aminopolyols 22, by employing the galactose oxidase F 2 variant (GOase F 2 ) to trigger the cyclisation (Scheme 4c). [12] The N-Cbz protected hemiaminal cyclic products 15, 20, and 21 (Scheme 4a-c) are all stable compounds that were often isolated as a mixture of hemiaminal and hemiacetal anomers. In all cases, the chemical reduction of the anomeric mixture, by means of hydrogenation over Pd/C, convergently provided the desired iminosugars 18, 23, and 24 as sole reduction products, most likely via an imine intermediate.…”