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Synlett 1997; 1997(Sup. I): 485-487
DOI: 10.1055/s-1997-940277
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Glucopyranose Spirohydantoins: Specific Inhibitors of Glycogen Phosphorylase

Carmen de la Fuente, Thomas M. Krülle, Kimberley A. Watson, Mary Gregoriou, Louise N. Johnson, Katerina E. Tsitsanou, Spyros E. Zographos, Nikos G. Oikonomakos, George W. J. Fleet*
  • *Dyson Perrins Laboratory, Oxford Centre for Molecular Sciences, South Parks Road, Oxford OX1 3QY, UK, E-mail george.fleet@dyson-perrins.oxford.ac.uk
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Publication Date:
12 April 2006 (online)

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A short synthesis of the spirohydantoin of glucopyranose 1β [a potent and specific inhibitor of glycogen phosphorylase], together with its inactive anomer 1α, from a readily available heptonolactone is described; this is the first synthesis of a spirohydantoin of a pyranose in which the pyranose ring is formed after the hydantoin ring.

hydantocidin - glycogen phosphorylase - enzyme inhibition - hydantoin - lactone