Premium
The Synthesis of Imidazol Sugars Which Mimic Cyclic Carboxonium Ions Formed During the Glycosidase‐Catalysed Hydrolysis of Oligo and Polysaccharides
Author(s) -
Streith Jacques,
Rudyk Hélène,
Tschamber Théophile,
Tarnus Céline,
Strehler Christiane,
Deredas Dariusz,
Frankowski Andrzej
Publication year - 1999
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/(sici)1099-0690(199904)1999:4<893::aid-ejoc893>3.0.co;2-#
Subject(s) - chemistry , hydrolysis , glycoside hydrolase , polysaccharide , organic chemistry , combinatorial chemistry , stereochemistry
Some naturally occurring carbohydrates, of which several hydroxy groups had been selectively protected, were condensed with formamidine to give the expected imidazole derivatives in the D ‐arabino ( 9 ), D ‐lyxo ( 12 ), L ‐xylo ( 17 ), D ‐threo ( 21) , and in the L ‐ and D ‐erythro ( 24 ) series. Introduction of a strong leaving group at the remaining free alcohol function of these products led at once to intramolecular S N 2 cyclisation to the corresponding bicyclic aza sugar derivatives. This was followed by total deprotection to give the target aza sugars in the L ‐xylo ( 7 ), L ‐ribo ( 14 ), D ‐arabino ( 19 ), as well as in the D ‐threo ( 22 ) and the L ‐ and D ‐erythro ( 26 ) series. Inhibitory assays with four glycosidases showed that the D ‐arabino aza sugar 19 is the only potent inhibitor (for an α‐mannosidase of jack bean).