Tautomeric modification of GIcNAc-thiazoline

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

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


The potent OGIcNAcase (OGA) inhibitor GIcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (Xn = D3, F, N 3, OH, SMe, COCF3, CF3). Several functionalized GIcNAc-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.

Original languageEnglish (US)
Pages (from-to)2321-2324
Number of pages4
JournalOrganic letters
Issue number12
StatePublished - Jun 7 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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