Modifying the Regioselectivity of Glycosynthase Reactions Through Changes in the Acceptor*

Robert V. Stick; Keith A. Stubbs; Andrew G. Watts

doi:10.1071/CH04025

RESEARCH ARTICLE

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Modifying the Regioselectivity of Glycosynthase Reactions Through Changes in the Acceptor*

Robert V. Stick ^A ^B , Keith A. Stubbs ^A and Andrew G. Watts ^A

+ Author Affiliations

- Author Affiliations

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

^B Author to whom correspondence should be addressed (e-mail: rvs@chem.uwa.edu.au).

Australian Journal of Chemistry 57(8) 779-786 https://doi.org/10.1071/CH04025
Submitted: 4 February 2004 Accepted: 26 March 2004 Published: 10 August 2004

Abstract

Successful glycosynthase-mediated reactions have been performed on 6-O-benzyl-, 6-O-(4-nitrobenzyl)-, and 6-O-benzoyl-d-glucopyranose to give 1,2-β- and 1,3-β-d-glycosylated products; 4-O-benzyl-d-xylopyranose gave only a 1,2-β-glycosylated product. A rationale is presented for these rather unusual results.

^* Dedicated to the memory of Christian Pedersen.

Acknowledgments

We thank Professor Stephen Withers for the generous gift of the glycosynthase. K.A.S. thanks the University of Western Australia for the assistance of a Hackett Postgraduate Scholarship.

References

Modifying the Regioselectivity of Glycosynthase Reactions Through Changes in the Acceptor*

Abstract

Acknowledgments

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