Work

Interplay of Monosaccharide Configurations on the Deacetylation with Candida antarctica Lipase-B

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Configurational differences in monosaccharides determine the products and selectivity of the transesterification reaction with Candida antarctica lipase-B (CAL-B). The β-anomers of peresterified pyranose monosaccharides tend to yield anomeric deprotection products, while the α-anomers preferentially react at the sixth or fourth position. CAL-B differentiates between enantiomers, either reacting more rapidly with d -enantiomers of monosaccharides or having a different selectivity based on the enantiomer. Pivaloylated and benzoylated saccharides are the limits of the CAL-B transesterification reaction, while lower boiling point alcohols such as MeOH and EtOH can replace n -BuOH as the nucleophilic reagent. Finally, CAL-B can be successfully recycled in both long and short reaction time reactions.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c02582

Authors: Kaarel Erik Hunt, Annette Miller, Kristin Liias, Tatsiana Jarg, Kadri Kriis, Tõnis Kanger

Institution: Tallinn University of Technology

Language: English

Topic: Enzyme Catalysis and Immobilization

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Eesti Teaduste Akadeemia, Haridus- ja Teadusministeerium, Novozymes