Literature DB >> 17508759

Tautomeric modification of GlcNAc-thiazoline.

Spencer Knapp1, Mohannad Abdo, Kehinde Ajayi, Richard A Huhn, Thomas J Emge, Eun Ju Kim, John A Hanover.   

Abstract

The potent O-GlcNAcase (OGA) inhibitor GlcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (Xn = D3, F, N3, OH, SMe, COCF3, CF3). Several functionalized GlcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

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Year:  2007        PMID： 17508759     DOI： 10.1021/ol0706814

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  Chemical approaches to understanding O-GlcNAc glycosylation in the brain.

Authors:  Jessica E Rexach; Peter M Clark; Linda C Hsieh-Wilson
Journal:  Nat Chem Biol       Date:  2008-02       Impact factor: 15.040

Review 2.  The chemical neurobiology of carbohydrates.

Authors:  Heather E Murrey; Linda C Hsieh-Wilson
Journal:  Chem Rev       Date:  2008-05-02       Impact factor: 60.622

3.  Dynamic O-GlcNAcylation and its roles in the cellular stress response and homeostasis.

Authors:  Jennifer A Groves; Albert Lee; Gokben Yildirir; Natasha E Zachara
Journal:  Cell Stress Chaperones       Date:  2013-04-26       Impact factor: 3.667

4.  Mechanism, Structure, and Inhibition of O-GlcNAc Processing Enzymes.

Authors:  Tracey M Gloster; David J Vocadlo
Journal:  Curr Signal Transduct Ther       Date:  2010-01

5.  O-GlcNAcylation: a novel post-translational mechanism to alter vascular cellular signaling in health and disease: focus on hypertension.

Authors:  Victor V Lima; Christiné S Rigsby; David M Hardy; R Clinton Webb; Rita C Tostes
Journal:  J Am Soc Hypertens       Date:  2009 Nov-Dec

6.  OGA inhibition by GlcNAc-selenazoline.

Authors:  Eun Ju Kim; Dona C Love; Etzer Darout; Mohannad Abdo; Brian Rempel; Stephen G Withers; Paul R Rablen; John A Hanover; Spencer Knapp
Journal:  Bioorg Med Chem       Date:  2010-08-11       Impact factor: 3.641

7.  Inhibition of O-GlcNAcase using a potent and cell-permeable inhibitor does not induce insulin resistance in 3T3-L1 adipocytes.

Authors:  Matthew S Macauley; Yuan He; Tracey M Gloster; Keith A Stubbs; Gideon J Davies; David J Vocadlo
Journal:  Chem Biol       Date:  2010-09-24

8.  Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline.

Authors:  Dusan Hesek; Mijoon Lee; Takao Yamaguchi; Bruce C Noll; Shahriar Mobashery
Journal:  J Org Chem       Date:  2008-08-09       Impact factor: 4.354

Review 9.  O-linked beta-N-acetylglucosamine (O-GlcNAc): Extensive crosstalk with phosphorylation to regulate signaling and transcription in response to nutrients and stress.

Authors:  Chutikarn Butkinaree; Kyoungsook Park; Gerald W Hart
Journal:  Biochim Biophys Acta       Date:  2009-08-06

Review 10.  O-GlcNAcase: promiscuous hexosaminidase or key regulator of O-GlcNAc signaling?

Authors:  Jana Alonso; Marianne Schimpl; Daan M F van Aalten
Journal:  J Biol Chem       Date:  2014-10-21       Impact factor: 5.157
  10 in total

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