Investigation of the specificity of an alpha-L-arabinofuranosidase using C-2 and C-5 modified alpha-L-arabinofuranosides.
The synthesis of three novel glycosyl donors presenting the same scaffold as alpha-L-arabinofuranose but modified at the C-2 or C-5 positions has been achieved. Furthermore, chemoenzymatic syntheses using the alpha-L-arabinofuranosidase AbfD3 and these unnatural furanosides were investigated. The use of the novel p-nitrophenyl furanoside donors revealed that AbfD3 can perform transglycosylation with the C-5 deoxygenated donor but not with the C-2 modified one. These results emphasize the vital role for OH-2 in AbfD3 substrate recognition.
Lopez
Gérald
G
Ecole Nationale Supérieure de Chimie de Rennes, UMR CNRS 6226 Sciences Chimiques de Rennes, Equipe Synthèse Organique et Systèmes Organisés, Avenue du Général Leclerc, F-35700 Rennes, France.
Nugier-Chauvin
Caroline
C
Rémond
Caroline
C
O'Donohue
Michael
M
D000438:Alcohols / Q000737:chemistry; D002236:Carbohydrate Conformation; D002244:Carbon / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002855:Chromatography, Thin Layer / Q000379:methods; D004187:Disaccharides / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006031:Glycosylation; D007477:Ions; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry; D013379:Substrate Specificity; D014995:Xylosidases / Q000737:chemistry
D000438:Alcohols; D004187:Disaccharides; D005663:Furans; D007477:Ions; D002244:Carbon; D006026:Glycoside Hydrolases; D014995:Xylosidases; C019713:alpha-N-arabinofuranosidase; D010100:Oxygen