Stereomeric Pyrrolidinopentoses Bearing an Imidazole Ring − Synthesis, Chiroptical Properties, and Evaluation as Potential Sugar-Mimic Glycosidase Inhibitors

Autor: Hervé Siendt, Sylviane Kohler, Théophile Tschamber, Céline Tarnus, Dariusz Deredas, Jacques Streith, Andrzej Frankowski
Rok vydání: 2002
Předmět:
Zdroj: European Journal of Organic Chemistry. 2002:702-712
ISSN: 1099-0690
1434-193X
DOI: 10.1002/1099-0690(200202)2002:4<702::aid-ejoc702>3.0.co;2-y
Popis: The syntheses of the imidazolo-pyrrolidino-pentoses ent-2 (L-arabino), 3 (D-xylo), 4 (D-lyxo), ent-4 (L-lyxo), and 5 (D-ribo) are reported, completing the series of all eight possible stereomers. The corresponding five linear imidazolo sugar precursors were prepared by nucleophilic addition of C(4)-metallated imidazole derivatives to the appropriately configured and protected aldotetroses. Cyclisation of the resulting linear imidazolo-carbohydrates was performed by means of intramolecular Walden inversion processes, followed by deprotection to afford the five target imidazolo-sugars. Three of the four D-configured stereomers proved to be good to moderate glycosidase inhibitors, as determined by Michaelis−Menten kinetics.
Databáze: OpenAIRE
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