Synthesis and Biological Evaluation of 1,5-Dideoxy-1,5-iminoxylitol–Amino Acid Hybrids as Xylosidase Inhibitors*

Andreas J. Steiner; Arnold E. Stütz; Chris A. Tarling; Stephen G. Withers; Tanja M. Wrodnigg

doi:10.1071/CH09040

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Synthesis and Biological Evaluation of 1,5-Dideoxy-1,5-iminoxylitol–Amino Acid Hybrids as Xylosidase Inhibitors*

Andreas J. Steiner ^A , Arnold E. Stütz ^A , Chris A. Tarling ^B , Stephen G. Withers ^B and Tanja M. Wrodnigg ^A ^C

+ Author Affiliations

- Author Affiliations

^A Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.

^B Chemistry Department, University of British Columbia, 300-6174 University Boulevard, Vancouver, BC V6T 1Z3, Canada.

^C Corresponding author. Email: t.wrodnigg@tugraz.at

Australian Journal of Chemistry 62(6) 553-557 https://doi.org/10.1071/CH09040
Submitted: 19 January 2009 Accepted: 19 February 2009 Published: 10 June 2009

Abstract

1,5-Dideoxy-1,5-iminoxylitol–amino acid hybrids have been synthesized by cyclisation via a double reductive amination of xylo-pentodialdose and the respective amino groups of lysine as well as serine components. Further modification with aromatic substituents gave access to lipophilic derivatives. Kinetic studies revealed that all compounds exhibited better inhibitory properties against β-xylosidase from Thermoanaerobacterium sacharolyticum than the parent iminosugar.

^* Dedicated to Professor Robert V. Stick.

Acknowledgements

Financial support by the Austrian Fonds zur Förderung der Wissenschaftlichen Forschung (FWF), Vienna (Project P18998-N17), as well as by the Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged.

References

Synthesis and Biological Evaluation of 1,5-Dideoxy-1,5-iminoxylitol–Amino Acid Hybrids as Xylosidase Inhibitors*

Abstract

Acknowledgements

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