Neodisaccharide diglycosyl compounds: Ethers, thioethers and selenoethers. A survey of their synthesis and biological activity

Abstract

This article gives an account of the area of nonglycosidically linked neodisaccharide compounds consisting of two monosaccharides linked by formal condensation without using the anomeric centre, i.e. by ether bonds, and also their thioether and selenoether counterparts. Synthetic methods and biological relevance are covered.

Sweet Selenium: Synthesis and Properties of Selenium-Containing Sugars and Derivatives

“…Five years later, Mori Pseudodisaccharides, where selenium links the two monosaccharides in a position different from the anomeric one, were also obtained [88,89] and the synthetic methods for their preparation were recently collected in a review article in which also their biological properties are discussed. Briefly, selenopseudo disaccharides were studied as lectin binders, that may have a number of potential therapeutic applications such as antibacterial (inhibitors of bacterial lectins), anti-inflammatory (selectins inhibitors), or anticancer (galectins inhibitors) agents [90].…”

Chemical Modification of Polysaccharides

“…It is perhaps worth noting that in monosaccharides, the introduction of thiol nucleophiles at the secondary positions of pyranosides by triflate displacement is relatively trivial [117], but related work has not been done to date in polysaccharides. Also in monosaccharides, selenoethers have been introduced in a protecting-group-minimised approach, similar to those described here for thioethers [118].…”

pKa‐Determination and Conformational Studies by NMR Spectroscopy of D‐Altrose‐Containing and other Pseudodisaccharides as Glycosidase Inhibitor Candidates

“…It was recently shown that neutral non-glycosidically linked thioether and ether pseudodisaccharides [3] can act as ligands for lectins with binding affinities similar to those of natural disaccharides in some cases. [4] A hypothesis to explain this behaviour is that one monosaccharide can mimic another monosaccharide by binding to a protein in such a way that some key interactions, e.g., hydrogen bonding or hydrophobic interactions, are conserved.…”

“…[42] Calculations of the populations of the ring conformational states and ω torsion angles were performed using the Solver function of Microsoft Excel ® with the calculated coupling constants. R values were calculated for each 3 J H,H coupling, in accordance with Equation (3). The average of the R J values, for each compound, was set to be minimised in the Solver function by altering the populations of the conformational states of the sugar rings and the ω torsion angles.…”