Tetrahedron p. 3093 - 3106 (1988)
Update date:2022-08-03
Topics:
Maryanoff, Bruce E.
Reitz, Allen B.
Nortey, Samuel O.
Various D-furanose monosaccharides were synthesized as possible inhibitors of the gluconeogenic enzyme fructose 1,6-bisphosphatase.These included sulfamate, phosphoramidate, and epoxy analogues of the natural substrate, fructose 1,6-diphosphate (1), and arabinose and ribose analogues of a natural inhibitor, fructose 2,6-diphosphate (2).NMR studies were conducted to establish the stereochemistry of phosphate displacement at Cl in the synthesis of arabinose 1-phosphate derivatives. β-Ribose 1,5-diphosphate (35b) was prepared with >95 percent stereoselectivity.
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