Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase.
Two sulfonium salts of 1,4-anhydro-4-thio-D-galactitol, with structures related to the known sulfonium salt glycosidase inhibitor, salacinol, have been synthesized as potential inhibitors of UDP-galactopyranose mutase. The synthetic strategy relies on the alkylation reaction of 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thio-D-galactitol at the sulfur atom with 2,4-O-benzylidene-D- or -L-erythritol-1,3-cyclic sulfate. In each case, the reaction proceeded stereoselectively to yield only one stereoisomer at the stereogenic sulfur atom. The effect of the polar solvent, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), in promoting high-yielding reactions is highlighted. The target compounds are then obtained by hydrogenolysis.
Ghavami
Ahmad
A
Department of Chemistry, Simon Fraser University, British Columbia, V5A 1S6, Burnaby, Canada.
Chen
Joan Jo-wen
JJ
Mario Pinto
B
B
D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D013452:Sulfonium Compounds / Q000138:chemical synthesis*
D004791:Enzyme Inhibitors; D013452:Sulfonium Compounds; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase