The conformational characteristics of abasic 1-deoxy sugars 1,2, and 3 and pentofuranose moieties in 2‘,3‘dideoxy-[ddA (6), ddG (7), ddC (S)], 2’-deoxy-[dA (9), dG (lo), dC (ll)], and ribo-@-D-nucleosides [Ade (12), Gua (13), Cyt (14)] were established through the analysis of vicinal proton-proton coupling constants extracted from their 500-MHz lH-NMR spectra recorded at 20 K intervals in the t...

The first total synthesis of dinemasone A, a bioactive metabolite with a spiroketal moiety, is described. The main strategy for the construction of the spiroketal unit involves a double intramolecular hetero-Michael addition (DIHMA) of an ynone moiety. The thus obtained axial-equatorial mono anomeric spiroketal, on spiroepimerization with ZnBr(2), was converted into the requisite axial-axial do...

In tumoral cells derived from the insulin-producing rat cell line RINm5F, both low- and high-Km glucose-phosphorylating enzymic activities were present. The hexokinase-like enzyme was inhibited by glucose 6-phosphate and displayed a greater affinity for but lower maximal velocity with alpha-D-glucose than beta-D-glucose. A comparable anomeric behavior of hexokinase was observed in breast cancer...

In this note, an hydrozirconation/bromination/Michaelis-Arbuzov sequence was developped to introduce a trimethylene phosphonate unit on ketopyranosides. Performed polyfunctional substrates bearing orthogonal protecting groups, new approach provided straightforward entry towards large diversity of glycophosphomimetics having quaternary anomeric position.

For the first time in natural O-glycosides, a large amount of non-exo-anomeric conformation is experimentally detected, in solution.