906562-60-5Relevant academic research and scientific papers
Synthesis, biological evaluation, wac and NMR studies of s-galactosides and non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties
Ramos-Soriano, Javier,Niss, Ulf,Angulo, Jesus,Angulo, Manuel,Moreno-Vargas, Antonio J.,Carmona, Ana T.,Ohlson, Sten,Robina, Inmaculada
supporting information, p. 17989 - 18003 (2014/01/17)
The synthesis of several non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties is reported. Some of them have been linked to D-galactose through a stable and well-tolerated S-glycosidic bond. They represent a novel type of non-hydrolyzable bidentate ligand featuring galactose and polyhydroxyalkylfuroic esters as pharmacophoric residues, thus mimicking the GM1 ganglioside. The affinity of the new compounds towards cholera toxin was measured by weak affinity chromatography (WAC). The interaction of the best candidates with this toxin was also studied by saturation transfer difference NMR experiments, which allowed identification of the binding epitopes of the ligands interacting with the protein. Interestingly, the highest affinity was shown by non-carbohydrate mimics based on a polyhydroxyalkylfuroic ester structure. No carbs here: Saturation transfer difference (STD) NMR studies of bidentate ligands of cholera toxin (see figure, WAC = weak affinity chromatography) show the methylfuran moiety as the main contact point in the interaction with the toxin. Several polyhydroxyalkylfuroate-based structures are synthesized and analyzed and show similar or even better affinity than the bidentate ligands. They constitute the first examples of non-carbohydrate ligands for cholera toxin. Copyright
New methodology for the stereoselective synthesis of a-furfurylamines from sugars: Application to the synthesis of furyl amino acids and 3-Furylisoserines
Molina, Lidia,Moreno-Clavijo, Elena,Moreno-Vargas, Antonio J.,Carmona, Ana T.,Robina, Inmaculada
experimental part, p. 3110 - 3119 (2010/08/19)
The synthesis of two new furyl amino acids as rigid isosteres of the dipeptides (D)-H-Ser-(D, L)-Thr-OH and (L)-H-Ser-(D, L)Thr-OH is presented. The developed synthetic methodology starts from D-xylose and D-arabinose and makes use of trihydroxypropylfura
