title: Spirohydantoins from D-ribose as new potent enzymatic inhibitors.
abstract: Anomeric spirohydantoin derivatives from monosaccharides are known for various biological properties. We describe herein the synthesis of the 3-spirohydantoin derivatives of D-allose and D-ribose. The key step is the stereoselective glyco-alpha-aminonitrile formation from ulose derivatives of D-glucose and D-xylose using titanium tetra-isopropoxide as a mild and efficient catalyst. Target compounds were synthesized from these intermediates. The glucidic moiety was partially or totally deprotected under acidic conditions. These new heterocyclic monosaccharidic derivatives are potent glycogen phosphorylase inhibitors.
authors.affiliation: Laboratoire des Glucides, Université de Picardie, Amiens, France.
authors.forename: A
authors.initials: A
authors.lastname: Nguyen
authors.forename: P
authors.initials: P
authors.lastname: Villa
authors.forename: G
authors.initials: G
authors.lastname: Ronco
authors.forename: D
authors.initials: D
authors.lastname: Postel
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006827:Hydantoins / Q000138:chemical synthesis*; D012266:Ribose / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004791:Enzyme Inhibitors; D006827:Hydantoins; D013141:Spiro Compounds; D012266:Ribose