Design and Synthesis of 2‑Acetamido-2,3-dideoxythiodisaccharides
via Diastereoselective Conjugate Addition to Sugar Enone O‑Acetyl Oximes. Galactosidase Inhibition Studies
posted on 2018-09-17, 04:37authored byLucas Dada, Verónica
E. Manzano, Oscar Varela
The
key step in a new synthesis of 2-acetamido-2,3-dideoxy-(1→4)-thiodisaccharides
was the conjugate addition of a 1-thiogalactose derivative to E and Z acetyl oximes derived from sugar
enones. This reaction was shown to be completely diastereoselective
for both the formation of the thioglycosidic linkage and the configuration
of acetyl oxime. The thiodisaccharides have been designed as inhibitors
of the β-galactosidase from E. coli, and they
have been shown to successfully meet such requirements.