Biocatalytic Oxidation in Continuous Flow for the Generation of Carbohydrate Dialdehydes

Cosgrove, Sebastian C.; Mattey, Ashley P.; Riese, Michel; Chapman, Michael R.; Birmingham, William R.; Blacker, A. John; Kapur, Nikil; Turner, Nicholas J.; Flitsch, Sabine L.

Abstract

Galactose Oxidase (GOase) has been used for the scalable and selective C-6′ oxidation of lactose, a waste material from the dairy industry. Generation of the 6′-oxo lactose was achieved with full conversion in batch mode at milligram scale, but further scale-up to gram quantities proved to be challenging because of requirements for high enzyme concentrations and limitation in oxygen cosubstrate availability. To overcome these issues, a continuous-flow system was developed for the bio-oxidation of lactose yielding multigram quantities of product. Using the variant GOase F2, terminal selective oxidations were also observed on a range of oligoglucosides such as maltose. The carbohydrate dialdehydes that were obtained by this highly selective oxidation were chemically further functionalized, establishing the biooxidation as a route to valorize cheap carbohydrates, including waste materials, for building blocks of polymers.

Citation

Cosgrove, S. C., Mattey, A. P., Riese, M., Chapman, M. R., Birmingham, W. R., Blacker, A. J., …Flitsch, S. L. (2019). Biocatalytic Oxidation in Continuous Flow for the Generation of Carbohydrate Dialdehydes. ACS catalysis, 9(12), 11658-11662. https://doi.org/10.1021/acscatal.9b04819

• Journal Article Type: Article
• Online Publication Date: Nov 15, 2019
• Publication Date: Dec 6, 2019
• Deposit Date: Jun 14, 2023
• Journal: ACS Catalysis
• Electronic ISSN: 2155-5435
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 9
• Issue: 12
• Pages: 11658-11662
• DOI: https://doi.org/10.1021/acscatal.9b04819
• Keywords: Catalysis; General Chemistry