Literature DB >> 18996021

1-Deoxygalactonojirimycin-lysine hybrids as potent D-galactosidase inhibitors.

Andreas J Steiner1, Georg Schitter, Arnold E Stütz, Tanja M Wrodnigg, Chris A Tarling, Stephen G Withers, Katrin Fantur, Don Mahuran, Eduard Paschke, Michael Tropak.   

Abstract

Cyclization by double reductive amination of L-arabino-hexos-5-ulose with suitably protected D- as well as L-lysine derivatives provided 1-deoxygalactonojirimycin lysine hybrids without any observable epimer formation at C-5. Modifications on the lysine moiety by acylation gave access to lipophilic derivatives which exhibited excellent D-galactosidase inhibitory activities.

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Year:  2008        PMID： 18996021      PMCID： PMC2910748          DOI： 10.1016/j.bmc.2008.10.054

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  9 in total

1.  Powerful probes for glycosidases: novel, fluorescently tagged glycosidase inhibitors.

Authors:  A Hermetter; H Scholze; A E Stütz; S G Withers; T M Wrodnigg
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2.  Isofagomine- and 2,5-anhydro-2,5-imino-D-glucitol-based glucocerebrosidase pharmacological chaperones for Gaucher disease intervention.

Authors:  Zhanqian Yu; Anu R Sawkar; Lisa J Whalen; Chi-Huey Wong; Jeffery W Kelly
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3.  Fluorescently tagged iminoalditol glycosidase inhibitors as novel biological probes and diagnostics.

Authors:  Inge Lundt; Andreas J Steiner; Arnold E Stütz; Chris A Tarling; Stefan Ully; Stephen G Withers; Tanja M Wrodnigg
Journal:  Bioorg Med Chem       Date:  2005-11-07       Impact factor: 3.641

4.  The subunit and polypeptide structure of hexosaminidases from human placenta.

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Review 5.  Naturally occurring iminosugars and related compounds: structure, distribution, and biological activity.

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Journal:  Curr Top Med Chem       Date:  2003       Impact factor: 3.295

6.  Glycosidase profiling with immobilised glycosidase-inhibiting iminoalditols--a proof-of-concept study.

Authors:  Andreas J Steiner; Arnold E Stütz; Tanja M Wrodnigg; Chris A Tarling; Stephen G Withers; Albin Hermetter; Hannes Schmidinger
Journal:  Bioorg Med Chem Lett       Date:  2008-02-07       Impact factor: 2.823

7.  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.

Authors:  Peter Greimel; Herwig Häusler; Inge Lundt; Karen Rupitz; Arnold E Stütz; Chris A Tarling; Stephen G Withers; Tanja M Wrodnigg
Journal:  Bioorg Med Chem Lett       Date:  2006-02-14       Impact factor: 2.823

8.  Mechanism of Agrobacterium beta-glucosidase: kinetic studies.

Authors:  J B Kempton; S G Withers
Journal:  Biochemistry       Date:  1992-10-20       Impact factor: 3.162

9.  Iminoalditol-amino acid hybrids: synthesis and evaluation as glycosidase inhibitors.

Authors:  Andreas J Steiner; Arnold E Stütz; Chris A Tarling; Stephen G Withers; Tanja M Wrodnigg
Journal:  Carbohydr Res       Date:  2007-03-28       Impact factor: 2.104
  9 in total
  6 in total

1.  Fluorous iminoalditols act as effective pharmacological chaperones against gene products from GLB₁ alleles causing GM1-gangliosidosis and Morquio B disease.

Authors:  Katrin M Fantur; Tanja M Wrodnigg; Arnold E Stütz; Bettina M Pabst; Eduard Paschke
Journal:  J Inherit Metab Dis       Date:  2011-10-28       Impact factor: 4.982

2.  2-Acetamino-1,2-dideoxynojirimycin-lysine hybrids as hexosaminidase inhibitors.

Authors:  Andreas J Steiner; Georg Schitter; Arnold E Stütz; Tanja M Wrodnigg; Chris A Tarling; Stephen G Withers; Don J Mahuran; Michael B Tropak
Journal:  Tetrahedron Asymmetry       Date:  2009-05-01

3.  Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors.

Authors:  Georg Schitter; Elisabeth Scheucher; Andreas J Steiner; Arnold E Stütz; Martin Thonhofer; Chris A Tarling; Stephen G Withers; Jacqueline Wicki; Katrin Fantur; Eduard Paschke; Don J Mahuran; Brigitte A Rigat; Michael Tropak; Tanja M Wrodnigg
Journal:  Beilstein J Org Chem       Date:  2010-03-01       Impact factor: 2.883

4.  The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations.

Authors:  Cornelia Hojnik; Anne Müller; Tobias-Elias Gloe; Thisbe K Lindhorst; Tanja M Wrodnigg
Journal:  European J Org Chem       Date:  2016-06-27

5.  Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid.

Authors:  Mario J Simirgiotis; Javier Vallejos; Carlos Areche; Beatriz Sepúlveda
Journal:  Molecules       Date:  2014-11-26       Impact factor: 4.411

6.  Exploiting angled thin film vortex microfluidics for expeditious syntheses of iminosugars.

Authors:  Jeremy Duczynski; Colin L Raston; Keith A Stubbs
Journal:  RSC Adv       Date:  2022-08-17       Impact factor: 4.036
  6 in total

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