Work

Synthetic Access to l -Guluronic Acid via Fluorine-Directed C-5 Epimerization

Year: 2024

Type: article

Abstract: L-Guluronic acid is integral to the structures of alginates and to the pathogenesis of Pseudomonas aeruginosa. The exploitation of this hexose in both existing and new contexts is, however, limited by its prohibitively high commercial cost. We report on a short and efficient synthetic route to an L-GulA building block from a simple D-mannose thioglycoside. In this synthesis, the fluorine-directing effect is exploited to achieve a stereoselective C-5 epimerization. DFT calculations illuminate the substituent effects which operate to confer this selectivity.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01257

Authors: Nicholas W. See, Norbert Wimmer, Guoqing Zhang, Elizabeth H. Krenske, Vito Ferro

Institution: The University of Queensland

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: University of Queensland, Australian Research Council

Award: Opening Up Access to L-Sugars through a Synergy of Experiment and Theory