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Stereoisomeric Imidazolo‐Pentoses − Synthesis, Chiroptical Properties, and Evaluation as Glycosidase Inhibitors
Author(s) -
Tschamber Théophile,
Siendt Hervé,
Boiron Arnaud,
Gessier François,
Deredas Dariusz,
Frankowski Andrzej,
Picasso Sylviane,
Steiner Heinz,
Aubertin AnneMarie,
Streith Jacques
Publication year - 2001
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(200104)2001:7<1335::aid-ejoc1335>3.0.co;2-z
Subject(s) - chemistry , stereochemistry , enantiomer , intramolecular force , nucleophile , imidazole , sn2 reaction , nucleophilic substitution , organic chemistry , catalysis
The syntheses of all four imidazolo‐piperidino‐pentoses in the L ‐series ent ‐ 2 to ent ‐ 5 , and of three out of the four possible stereomers in the D ‐series 3 , 4 , and 5 , are reported. The linear imidazolo sugar precursors were prepared, either by double condensation of formamidine with protected aldohexoses, or by nucleophilic addition of a lithiated imidazole derivative to protected aldotetroses. Cyclisation of these linear imidazolo‐carbohydrates was performed by intramolecular S N 2 reactions. These were followed by deprotection to the target molecules. The four pairs of opposite enantiomers showed pronounced mirror‐image‐type Cotton effects in their CD spectra. All stereomers of the D ‐series show a negative rotatory power ([α] D ), while the stereomers of the L ‐series show a positive one. None of the eight imidazolo sugars inhibited the replication of HIV‐1. Some of them proved to be rather selective but only moderately potent inhibitors of α‐glycosidases, as determined by Michaelis‐Menten kinetics.