Tautomeric modification of GlcNAc-thiazoline |
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| Authors: | Knapp Spencer Abdo Mohannad Ajayi Kehinde Huhn Richard A Emge Thomas J Kim Eun Ju Hanover John A |
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| Institution: | Department of Chemistry and Chemical Biology, Rutgers-The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA. spencer.knapp@rutgers.edu |
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| 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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