Synthesis of Some Glycosylated Derivatives of 2-Deoxy-2-fluoro-β-laminaribiosyl Fluoride: Another Success for Glycosynthases

Adrian Scaffidi; Robert V. Stick; Keith A. Stubbs

doi:10.1071/CH06394

RESEARCH ARTICLE

Previous Contents Vol 60(1)

Synthesis of Some Glycosylated Derivatives of 2-Deoxy-2-fluoro-β-laminaribiosyl Fluoride: Another Success for Glycosynthases

Adrian Scaffidi ^A , Robert V. Stick ^A ^B and Keith A. Stubbs ^A

+ Author Affiliations

- Author Affiliations

^A Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley WA 6009, Australia.

^B Corresponding author. Email: rvs@chem.uwa.edu.au

Australian Journal of Chemistry 60(1) 83-88 https://doi.org/10.1071/CH06394
Submitted: 25 October 2006 Accepted: 4 December 2006 Published: 29 January 2007

Abstract

The synthesis of 4,6-di-O-acetyl-2-deoxy-2-fluoro-3-O-(tetra-O-acetyl-β-d-glucopyranosyl)-β-d-glucosyl fluoride is described. Upon deacetylation and treatment with α-d-glucopyranosyl fluoride in the presence of a glycosynthase, three products, all 2-deoxy-2-fluoro-β-glycosyl fluorides, could be isolated: a trisaccharide, a tetrasaccharide, and a pentasaccharide. An attempt to convert a trisaccharide glycal into a related difluoride, employing Selectfluor, is also reported.

Acknowledgments

We again thank Steve Withers for the generous supply of a range of glycosynthases, without which this work would not have been possible. K.A.S. thanks the University of Western Australia for the assistance of a Hackett Postgraduate Scholarship.

References

^A Some of the ring protons could not be unambiguously assigned.

Synthesis of Some Glycosylated Derivatives of 2-Deoxy-2-fluoro-β-laminaribiosyl Fluoride: Another Success for Glycosynthases

Abstract

Acknowledgments

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