'Click'-xylosides as initiators of the biosynthesis of glycosaminoglycans: Comparison of mono-xylosides with xylobiosides.
Different mono-xylosides and their corresponding xylobiosides obtained by a chemo-enzymatic approach featuring various substituents attached to a triazole ring were probed as priming agents for glycosaminoglycan (GAG) biosynthesis in the xylosyltransferase-deficient pgsA-745 Chinese hamster ovary cell line. Xylosides containing a hydrophobic aglycone moiety were the most efficient priming agents. Mono-xylosides induced higher GAG biosynthesis in comparison with their corresponding xylobiosides. The influence of the degree of polymerization of the carbohydrate part on the priming activity was investigated through different experiments. We demonstrated that in case of mono-xylosides, the cellular uptake as well as the affinity and the catalytic efficiency of β-1,4-galactosyltransferase 7 were higher than for xylobiosides. Altogether, these results indicate that hydrophobicity of the aglycone and degree of polymerization of glycone moiety were critical factors for an optimal priming activity for GAG biosynthesis.
CNRS UMR 7369, Matrice Extracellulaire et Dynamique Cellulaire, UFR de Médecine, Université de Reims Champagne Ardenne, Reims Cedex, France.|Laboratoire de Biochimie Médicale et Biologie Moléculaire, UFR de Médecine, Université de Reims Champagne Ardenne, Reims Cedex, France.
Aurore
A
Chatron-Colliet
Institut de Chimie Moléculaire de Reims (ICMR), CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, Université de Reims Champagne-Ardenne, Reims Cedex 2, France.|UMR614 Fractionnement des AgroRessources et Environnement, Université de Reims Champagne-Ardenne, Reims Cedex, France.|UMR614 Fractionnement des AgroRessources et Environnement, INRA, Reims Cedex, France.
Charlotte
C
Brusa
MolCelTEG Team and Glyco-Fluo platform (UMR 7365 and FR3209) Biopôle - Faculté de Médecine, UMR 7365 CNRS-Université de Lorraine, Vandoeuvre-lès-Nancy Cedex, France.
Isabelle
I
Bertin-Jung
MolCelTEG Team and Glyco-Fluo platform (UMR 7365 and FR3209) Biopôle - Faculté de Médecine, UMR 7365 CNRS-Université de Lorraine, Vandoeuvre-lès-Nancy Cedex, France.
Sandrine
S
Gulberti
MolCelTEG Team and Glyco-Fluo platform (UMR 7365 and FR3209) Biopôle - Faculté de Médecine, UMR 7365 CNRS-Université de Lorraine, Vandoeuvre-lès-Nancy Cedex, France.
Nick
N
Ramalanjaona
MolCelTEG Team and Glyco-Fluo platform (UMR 7365 and FR3209) Biopôle - Faculté de Médecine, UMR 7365 CNRS-Université de Lorraine, Vandoeuvre-lès-Nancy Cedex, France.
Sylvie
S
Fournel-Gigleux
CNRS UMR 7369, Matrice Extracellulaire et Dynamique Cellulaire, UFR de Médecine, Université de Reims Champagne Ardenne, Reims Cedex, France.|Laboratoire de Biochimie Médicale et Biologie Moléculaire, UFR de Médecine, Université de Reims Champagne Ardenne, Reims Cedex, France.
Stéphane
S
Brézillon
Institut de Chimie Moléculaire de Reims (ICMR), CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, Université de Reims Champagne-Ardenne, Reims Cedex 2, France.
Murielle
M
Muzard
Institut de Chimie Moléculaire de Reims (ICMR), CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, Université de Reims Champagne-Ardenne, Reims Cedex 2, France.
Richard
R
Plantier-Royon
UMR614 Fractionnement des AgroRessources et Environnement, Université de Reims Champagne-Ardenne, Reims Cedex, France.|UMR614 Fractionnement des AgroRessources et Environnement, INRA, Reims Cedex, France.
Caroline
C
Rémond
CNRS UMR 7369, Matrice Extracellulaire et Dynamique Cellulaire, UFR de Médecine, Université de Reims Champagne Ardenne, Reims Cedex, France.|Laboratoire de Biochimie Médicale et Biologie Moléculaire, UFR de Médecine, Université de Reims Champagne Ardenne, Reims Cedex, France.
Yanusz
Y
Wegrowski
D000818:Animals; D016466:CHO Cells; D003412:Cricetulus; D005700:Galactosyltransferases / Q000235:genetics / Q000378:metabolism; D006025:Glycosaminoglycans / Q000096:biosynthesis*; D006027:Glycosides / Q000737:chemistry* / Q000378:metabolism*; D006801:Humans; D010430:Pentosyltransferases / Q000235:genetics / Q000378:metabolism; D013329:Structure-Activity Relationship; D000097608:UDP Xylose-Protein Xylosyltransferase
D005700:Galactosyltransferases; D006025:Glycosaminoglycans; D006027:Glycosides; D010430:Pentosyltransferases; D000097608:UDP Xylose-Protein Xylosyltransferase; C010807:xylosides; C063053:xylosylprotein 4-beta-galactosyltransferase
click chemistry; enzymatic transglycosylation; glycosaminoglycans; xylobiosides; xylosides