Xyloside

03 May 2017 - Xylosides with anti-aging properties

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03 May 2017 - Xylosides with anti-aging properties

03 May 2017 - Xylosides with anti-aging properties

Abundant in the plant walls, beta-D-xylopyranose (D-Xyl) is present only in the animal kingdom within the glycosaminoglycans (GAG), macromolecules of the extracellular matrix involved in many biological functions. GAG biosynthesis is initiated from protein-bound D-Xyl used as a substrate by a galactosyl transferase (beta-Gal T7). This biosynthesis decreases with age leading to skin relaxation (wrinkles). Functionalized on the anomeric position, D-xyl mimics the D-Xyl-protein set and initiates the exogenous synthesis of GAG thus limiting the age-related synthesis decay.

Xylosides (functionalized D-Xyl) are conventionally synthesized by multi-stage chemical approaches. Our approach, carried out through a collaboration between FARE and ICMR (URCA), consisted in developing a simple 2-step synthesis pathway: an enzyme step followed by a click-chemistry step to access a library of xylosides and xylobiosides presenting various functional groups. The biological properties of xylosides and xylobiosides were studied in collaboration with MEDyC (URCA) and MolCelTEG (U. Lorraine) laboratories. Thus, we studied the ability of the various xylosides and xylobiosides to initiate the exogenous synthesis of GAG in the presence of cell cultures and showed that hydrophobic functional groups allowed obtaining improved synthesis of GAG. Compared to xylobiosides, increased cell entry is observed for xylosides and a higher catalytic efficiency of galactosyl transferase bGal T7 towards xylosides is obtained. All of our results allowed us to provide informations about the structure-biological properties of xylosides and xylobiosides

Read: Chatron-Colliet A, Brusa C, Bertin-Jung I, Gulberti S, Ramalanjaona N, Fournel-Gigleux S, Brezillon S, Muzard M, Plantier-Royon R, Rémond C, Wegrowski Y. 'Click'-xylosides as initiators of the biosynthesis of glycosaminoglycans: comparison of mono-xylosides with xylobiosides. Chemical Biology & Drug Design 2017, 89, 319-326. DOI

Contacts: Pr Caroline Rémond, caroline.remond@univ-reims.fr
                 Pr Richard Plantier-Royon, richard.plantier-royon@univ-reims.fr

Modification date : 06 June 2023 | Publication date : 02 May 2017 | Redactor : C. Rémond, G. Paës