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Stereomeric Pyrrolidinopentoses Bearing an Imidazole Ring − Synthesis, Chiroptical Properties, and Evaluation as Potential Sugar‐Mimic Glycosidase Inhibitors
Author(s) -
Tschamber Théophile,
Siendt Hervé,
Tarnus Céline,
Deredas Dariusz,
Frankowski Andrzej,
Kohler Sylviane,
Streith Jacques
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200202)2002:4<702::aid-ejoc702>3.0.co;2-y
Subject(s) - chemistry , imidazole , intramolecular force , stereochemistry , sugar , ring (chemistry) , glycoside hydrolase , nucleophile , organic chemistry , hydrolysis , catalysis
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.