The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases†

† This paper is dedicated to the memory of Jacques H. van Boom.

Abstract

Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa‐fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining α‐glucosidase from barley.

† This paper is dedicated to the memory of Jacques H. van Boom.

Keywords:

• Glycoside hydrolases
• Glycosyl transferases
• Cyclopropanes
• Inhibitors

Acknowledgments

K.A.S. would like to thank The University of Western Australia for a Hackett Postgraduate Scholarship. We thank Andrew Watts for helpful discussions, and Birte Svensson and Henrik Naested (Technical University of Denmark) for performing some of the inhibition studies.

Notes

† This paper is dedicated to the memory of Jacques H. van Boom.

* The designation H8/C8 has been arbitrarily assigned to the hydrogen and carbon atoms of the substituent at C‐4 of the cyclohexane.