Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor Original Research Article

The development of β-d-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because β-d-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared β-d-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated β-d-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-β-d-Galactofuranosyl-O-ethylthiourethane, N-β-d-galactofuranosyl-4-oxoimidazolidine-2-thione, N-β-d-galactofuranosyl-4-imidazoline-2-thione, and N-β-d-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo β-d-galactofuranosidase inhibitor.