Non-Stick Sugars: Synthesis of Difluorosugar Fluorides as Potential Glycosidase Inactivators

Brian P. Rempel; Stephen G. Withers

doi:10.1071/CH09223

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Non-Stick Sugars: Synthesis of Difluorosugar Fluorides as Potential Glycosidase Inactivators

Brian P. Rempel ^A and Stephen G. Withers ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, University of British Columbia, Vancouver, British Columbia V6T 1Z3, Canada.

^B Corresponding author. Email: withers@chem.ubc.ca

Australian Journal of Chemistry 62(6) 590-599 https://doi.org/10.1071/CH09223
Submitted: 15 April 2009 Accepted: 8 May 2009 Published: 10 June 2009

Abstract

Four new difluorosugar fluorides, 2-deoxy-2,5-difluoro-α-l-idopyranosyl fluoride, 1,5-difluoro-d-glucopyranosyl fluoride, 1,5-difluoro-l-idopyranosyl fluoride, and 2-deoxy-1,2-difluoro-d-glucopyranosyl fluoride, were synthesized from known precursors by a radical bromination/fluoride displacement sequence, followed by deprotection. The compounds were tested as time-dependent inactivators of the β-glucosidase from Agrobacterium sp. (Abg, EC 3.2.1.21) and, while they were shown to bind to the enzyme active site as reversible competitive inhibitors, the only time-dependent inactivation observed was traced to the presence of an extremely small amount (<0.1%) of a highly reactive contaminating impurity.

Acknowledgements

We wish to thank Dr Shouming He for assistance in the mass spectral analysis of Abg, and Ms Karen Rupitz for providing Abg. Financial support from the Canadian Institutes for Health Research (Team Grant funding) is gratefully acknowledged. B.P.R. also wishes to thank the Natural Sciences and Engineering Research Council (NSERC), the Michael Smith Foundation for Health Research and the University of British Columbia, Department of Chemistry, for funding.

References

Non-Stick Sugars: Synthesis of Difluorosugar Fluorides as Potential Glycosidase Inactivators

Abstract

Acknowledgements

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