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Synlett 1997; 1997(2): 211-213
DOI: 10.1055/s-1997-736
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Stereospecific Synthesis of Spirohydantoins of β-Glucopyranose: Inhibitors of Glycogen Phosphorylase

Thomas M. Krülle, Carmen de la Fuente, 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; The National Hellenic Research Foundation, 48, Vas, Constantinou Avenue, Athens 111635, Greece; Laboratory of Molecular Biophysics, The Rex Richards Building, South Parks Road, Oxford OX1 3QU, UK
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Publication Date:
31 December 2000 (online)

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A stereospecific synthesis of the spirohydantoin of glucopyranose 1β [a potent and specific inhibitor of glycogen phosphorylase (GP)] and of a number of spirohydantoin analogues thereof relies on the rigidity of a bicyclic lactone 2. The effects of these analogues on GP are reported.

The epimeric azides 1 may be transformed into the bicyclic intermediate 2 which is a divergent precursor for the stereospecific synthesis of β-spirohydantoins of glucopyranose 3 which were evaluated as inhibitors of glycogen phosphorylase.

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