Synthesis of new analogues of salacinol containing a pendant hydroxymethyl group as potential glycosidase inhibitors.
The synthesis of new analogues of the naturally occurring glycosidase inhibitor, salacinol, and its ammonium analogue, ghavamiol is described. These analogues contain an additional hydroxymethyl group at C-1, which was intended to form additional polar contacts within the active site of glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least hindered carbon atom of 2,4-O-benzylidene-l (or d)-erythritol 1,3-cyclic sulfate by 2,5-anhydro-1,3:4,6-di-O-benzylidene-2,5-dideoxy-5-thio (or 1,5-imino)-l-iditol.
Nasi
Ravindranath
R
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
Pinto
B Mario
BM
D001089:Arabinose / Q000138:chemical synthesis; D002240:Carbohydrate Sequence; D004791:Enzyme Inhibitors; D004896:Erythritol / Q000138:chemical synthesis; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D050113:Imino Furanoses / Q000138:chemical synthesis; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis*; D013402:Sugar Alcohols / Q000138:chemical synthesis*; D013431:Sulfates / Q000138:chemical synthesis*
C431728:1'-((1,4-dideoxy-1,4-iminoarabinitol)-4-N-ammonium)-1'-deoxyerythritol-3'-sulfate; D004791:Enzyme Inhibitors; D050113:Imino Furanoses; D000644:Quaternary Ammonium Compounds; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol; D001089:Arabinose; D006026:Glycoside Hydrolases; D004896:Erythritol