Synthesis of pentose-containing disaccharides using a thermostable alpha-L-arabinofuranosidase.

Carbohydr Res

Laboratoire de Technologie Enzymatique et Physico-chimie des Agroressources, UMR URCA/INRA FARE, 8, rue Gabriel Voisin, BP 316, F-51688 Reims, France.

Published: August 2004

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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.

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http://dx.doi.org/10.1016/j.carres.2004.04.017DOI Listing

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