Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades. Issue 57 (12th June 2020)

• Record Type: Journal Article
• Authors: Ford, Grayson J.; Kress, Nico; Mattey, Ashley P.; Hepworth, Lorna J.; Baldwin, Christopher R.; Marshall, James R.; Seibt, Lisa S.; Huang, Min; Birmingham, William R.; Turner, Nicholas J.; Flitsch, Sabine L.
• Is Part Of: Chemical communications. Volume 56:Issue 57(2020)
• Page Start: 7949
• Page End: 7952
• Publication Date: 2020-06-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc02976a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Synthesis of Cbz-protected 3-aminopiperidine and 3-aminoazepane using a multi-enzyme cascade consisting of galactose oxidase and imine reductase variants. Abstract : Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N -Cbz-protected l -ornithinol and l -lysinol to l -3- N -Cbz-aminopiperidine and l -3- N -Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.