Synthesis of pentose-containing disaccharides using a thermostable alpha-L-arabinofuranosidase.
To date, the enzymatically-catalysed synthesis of pentose-containing compounds has been limited to the production of oligo-beta-(1-->3) and oligo-beta-(1-->4)-linked xylopyranosides. To our knowledge, no such syntheses have involved arabinofuranose or, indeed, any other sugars in the furanose configuration. In this report, we describe the use of a thermostable alpha-L-arabinofuranosidase for the synthesis of p-nitrophenyl alpha-L-arabinofuranosyl-(1-->2)-alpha-L-arabinofuranoside, p-nitrophenyl beta-D-xylopyranosyl-(1-->2)-beta-D-xylopyranoside, p-nitrophenyl beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranoside and benzyl alpha-D-xylopyranosyl-(1-->2)-alpha-L-arabinofuranoside. Importantly, this latter compound is synthesised in a highly regiospecific reaction, which leads to the production of a single disaccharide.
Rémond
Caroline
C
Laboratoire de Technologie Enzymatique et Physico-chimie des Agroressources, UMR URCA/INRA FARE, 8, rue Gabriel Voisin, BP 316, F-51688 Reims, France.
Plantier-Royon
Richard
R
Aubry
Nathalie
N
Maes
Emmanuel
E
Bliard
Christophe
C
O'Donohue
Michael J
MJ
D001086:Arabinofuranosyluracil / Q000031:analogs & derivatives / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis; D006031:Glycosylation; D006868:Hydrolysis; D008969:Molecular Sequence Data; D010429:Pentoses / Q000737:chemistry*; D013696:Temperature; D013997:Time Factors
D004187:Disaccharides; D006027:Glycosides; D010429:Pentoses; D001086:Arabinofuranosyluracil; D006026:Glycoside Hydrolases; C019713:alpha-N-arabinofuranosidase