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Biologically active branched-chain aminocyclopentane tetraols from d-galactose

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Abstract

From 1,2;3,4-di-O-isopropylidene-d-galactopyranose, a series of highly functionalized branched-chain cyclopentanes was easily available. The initial partially protected cyclopentane tetraol is a versatile central intermediate and was exploited as subject to various highly regio- and stereoselective structural alterations with a view to prepare selective β-d-galactosidase inhibitors. In line with our findings on recently reported constitutional isomers featuring amino substituents, basic derivatives are medium activity inhibitors of β-d-galactosidases with side activities for β-glucosidases.

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Acknowledgements

Financial support by the Austrian Fonds zur Förderung der Wissenschaftlichen Forschung (FWF), Vienna, (Projects P 24815-B21 as well as P 30372-B21) is gratefully acknowledged. P. W. thanks the Austrian Academy of Sciences for a DOC grant (2017-2020). SGW thanks GlycoNet, the Canadian Network of Centres of Excellence in glycoscience, for financial support. MZ, MS, AW, PW, AES and TMW gratefully acknowledge support from NAWI Graz.

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Authors and Affiliations

  1. Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria

    Michael Schalli, Patrick Weber, Arnold E. Stütz, Andreas Wolfsgruber & Tanja M. Wrodnigg

  2. Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada

    Seyed A. Nasseri & Stephen G. Withers

  3. Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria

    Ana Torvisco Gomez & Philipp Müller

Authors
  1. Michael Schalli
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  2. Patrick Weber
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  3. Seyed A. Nasseri
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  4. Ana Torvisco Gomez
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  5. Philipp Müller
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  6. Arnold E. Stütz
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  7. Stephen G. Withers
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  8. Andreas Wolfsgruber
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  9. Tanja M. Wrodnigg
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Correspondence to Arnold E. Stütz.

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Dedicated to Professor Dr. Heinz Falk on the happy occasion of his 80th birthday anniversary.

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Schalli, M., Weber, P., Nasseri, S.A. et al. Biologically active branched-chain aminocyclopentane tetraols from d-galactose. Monatsh Chem 150, 861–870 (2019). https://doi.org/10.1007/s00706-019-02428-0

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  • DOI: https://doi.org/10.1007/s00706-019-02428-0

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