Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications

Abstract

Thiosugars, containing a sulfur atom as heteroatom or a disaccharide linked via a sulfur bridge, possess unique physicochemical properties such as water solubility, which differs from conventional functionalized monosaccharides. The differences in biological activities between thiosugars and their oxygen analogs depend on geometric, conformational, and flexibility differences. They depend also on their electronic differences, the sulfide function being less electronegative and more polarizable than the ethereal moiety. Many functionalized thiosugars occur naturally and are potential targets for the development of carbohydrate-based therapeutics. Among the few new examples of the potential new targets are salacinol and kotalanol, tagetitoxin, thiolactomycin and analogues, mycothiol and analogues, and S-nitrosothiols. These new developments and representative examples of functionalized thiosugar prototypes as potential new targets are presented in this mini review.

A Straightforward and General Strategy Towards 1,5‐Dithio‐1‐enopyranosides

“…[4] Owing to their interesting biological activities, these compounds have recently attracted considerable interest from chemists and biochemists. [5] In particular, 1,5-dithio--xylopyranose-derived glycosides like 1 ( Figure 1) have proved to be orally active anti-thrombotic agents. [6] Figure 1.…”

Enzymatic and Organocatalyzed Asymmetric Aldolization Reactions for the Synthesis of Thiosugar Scaffolds

“…Preparation of NaIO 4 -SiO 2 : Following the conditions described by Zang et al, [1] NaIO 4 (45.3 g, 212.0 mmol) was dissolved in water (140 mL) in a 2 L round-bottomed flask. The solution was heated to reflux before the addition of silica gel (SiO 2 , 230-400 mesh, 250 g) with vigorous shaking.…”

“…[1,2] Sulfur-in-the-ring free sugars differ greatly from conventional oxygen-in-the-ring sugars, as replacement of the ring oxygen atom by a sulfur heteroatom gives them unique physicochemical properties. [1,[2][3][4] Synthetic 5-thioglycosides, i.e. glycosides with sulfur in place of oxygen in the ring, have been shown to be exoglycosidase resistant.…”

Melanoma Cell Factory for Glycolipid Production

“…Sulfur containing compounds have various applications in the pharmaceutical industry and in synthetic chemistry as glycosyl donors for the synthesis of complex oligisaccharides (Castaneda, 2007;Codee, 2005;Garegg, 1997;Krag, 2010;Witzak, 2005). Thiolactosides having a lactose moiety linked to a hydrophobic dodecyl aglycon unit via S-glycosidic bond have also been prepared and administered into mouse melanoma B16 cells (Mori et al, 2011).…”