198271-89-5Relevant academic research and scientific papers
Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor
Marino, Carla,Herczegh, Pal,De Lederkremer, Rosa M
, p. 123 - 128 (2007/10/03)
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.
Reactions of per-O-benzoyl-β-D-galf isothiocyanate, a chiral resolving agent
Marino, Carla,Varela, Oscar,De Lederkremer, Rosa M.
, p. 16009 - 16016 (2007/10/03)
Tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of recemic primary and secondary mines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1.
