A Biomimetic Synthetic Receptor Selectively Recognising Fucose in Water. Issue 26 (19th April 2018)

• Record Type: Journal Article
• Authors: Francesconi, Oscar; Martinucci, Marco; Badii, Lorenzo; Nativi, Cristina; Roelens, Stefano
• Is Part Of: Chemistry. Volume 24:Issue 26(2018)
• Page Start: 6828
• Page End: 6836
• Publication Date: 2018-04-19
• Subjects: carbohydrates -- hydrogen bonds -- macrocycles -- molecular recognition -- receptors; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201800390
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Carbohydrate recognition in water by biomimetic receptors is an attractive, but very challenging goal. Despite advances achieved in glucose recognition, little or no success has been obtained in the recognition of other saccharidic epitopes of paramount importance in biological processes. Herein, the unprecedented recognition of fucose in water by an artificial receptor that shows affinities closely comparable to those of several lectins is reported. The receptor has been constructed by assembling a hydrogen‐bonding element (carbazole), a hydrophobic aromatic moiety (anthracene), and a water‐solubilising function (phosphonate) into a macrocyclic structure to provide the appropriate binding geometry. The described receptor binds fucose with sub‐millimolar affinity in water at physiological pH; this shows that enthalpic binding can be ascribed to hydrogen bonding to saccharidic hydroxy groups and to CH−π interactions between the sugar backbone and aromatic moieties. Experimental NOE contacts coupled to conformational search calculations return a picture of a binding site in which fucose assumes a staggered orientation reminiscent of that shown by fucose when bound to the Ralstonia solanacearum lectin (RSL). Abstract : Focus on fucose : A synthetic receptor constructed through the assembly of a hydrogen‐bonding element (carbazole), a hydrophobic aromatic moiety (anthracene), and a water‐solubilising function (phosphonate) into a macrocyclic structure provides the appropriate geometry to bind fucose selectively (see figure) with sub‐millimolar affinity in water at physiological pH.