Literature DB >> 22328804

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

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

Abstract

Cyclisation by double reductive amination of 2-acetamino-2-deoxy-D-xylo-hexos-5-ulose with N-2 protected L-lysine derivatives provided 2-acetamino-1,2-dideoxynojirimycin derivatives without any observable epimer formation at C-5. Modifications on the lysine moiety gave access to lipophilic derivatives that exhibited improved hexosaminidase inhibitory activities.

Entities:  

Year:  2009        PMID： 22328804      PMCID： PMC3276585          DOI： 10.1016/j.tetasy.2009.02.015

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  22 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
Journal:  Bioorg Med Chem Lett       Date:  2001-05-21       Impact factor: 2.823

2.  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

3.  High-throughput screening for human lysosomal beta-N-Acetyl hexosaminidase inhibitors acting as pharmacological chaperones.

Authors:  Michael B Tropak; Jan E Blanchard; Stephen G Withers; Eric D Brown; Don Mahuran
Journal:  Chem Biol       Date:  2007-02

Review 4.  Naturally occurring iminosugars and related compounds: structure, distribution, and biological activity.

Authors:  Naoki Asano
Journal:  Curr Top Med Chem       Date:  2003       Impact factor: 3.295

5.  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

6.  Synthesis and high-throughput screening of N-acetyl-beta-hexosaminidase inhibitor libraries targeting osteoarthritis.

Authors:  Junjie Liu; Mehdi M D Numa; Haitian Liu; Shi-Jung Huang; Pamela Sears; Alexander R Shikhman; Chi-Huey Wong
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

7.  Chitin induces accumulation in tissue of innate immune cells associated with allergy.

Authors:  Tiffany A Reese; Hong-Erh Liang; Andrew M Tager; Andrew D Luster; Nico Van Rooijen; David Voehringer; Richard M Locksley
Journal:  Nature       Date:  2007-04-22       Impact factor: 49.962

8.  A general synthesis of iminosugars.

Authors:  Ciaran McDonnell; Linda Cronin; Julie L O'Brien; Paul V Murphy
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354

9.  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

10.  Identification of pharmacological chaperones for Gaucher disease and characterization of their effects on beta-glucocerebrosidase by hydrogen/deuterium exchange mass spectrometry.

Authors:  Michael B Tropak; Gregory J Kornhaber; Brigitte A Rigat; Gustavo H Maegawa; Justin D Buttner; Jan E Blanchard; Cecilia Murphy; Steven J Tuske; Stephen J Coales; Yoshitomo Hamuro; Eric D Brown; Don J Mahuran
Journal:  Chembiochem       Date:  2008-11-03       Impact factor: 3.164
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  6 in total

1.  Fluorous iminoalditols: a new family of glycosidase inhibitors and pharmacological chaperones.

Authors:  Georg Schitter; Andreas J Steiner; Gerit Pototschnig; Elisabeth Scheucher; Martin Thonhofer; Chris A Tarling; Stephen G Withers; Katrin Fantur; Eduard Paschke; Don J Mahuran; Brigitte A Rigat; Michael B Tropak; Carina Illaszewicz; Robert Saf; Arnold E Stütz; Tanja M Wrodnigg
Journal:  Chembiochem       Date:  2010-09-24       Impact factor: 3.164

2.  sp2-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease.

Authors:  Manuel González-Cuesta; Irene Herrera-González; M Isabel García-Moreno; Roger A Ashmus; David J Vocadlo; José M García Fernández; Eiji Nanba; Katsumi Higaki; Carmen Ortiz Mellet
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.756

3.  Inhibitors for Bacterial Cell-Wall Recycling.

Authors:  Takao Yamaguchi; Blas Blázquez; Dusan Hesek; Mijoon Lee; Leticia I Llarrull; Bill Boggess; Allen G Oliver; Jed F Fisher; Shahriar Mobashery
Journal:  ACS Med Chem Lett       Date:  2012-01-19       Impact factor: 4.345

4.  2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride-oxy-l-xylitol (N-benzyl-l-XYLNAc).

Authors:  Sarah F Jenkinson; Elizabeth V Crabtree; Andreas F G Glawar; Terry D Butters; George W J Fleet; David J Watkin
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-24

5.  The development of selective inhibitors of NagZ: increased susceptibility of Gram-negative bacteria to β-lactams.

Authors:  Keith A Stubbs; John-Paul Bacik; G Evan Perley-Robertson; Garrett E Whitworth; Tracey M Gloster; David J Vocadlo; Brian L Mark
Journal:  Chembiochem       Date:  2013-09-05       Impact factor: 3.164

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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