Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-D-tagatose from L-fucose and of 6-deoxy-D-tagatose from D-fucose using Enterobacter agglomerans strain 221e

摘要

1-Deoxy-D-tagatose was produced by the hydrogenation of 6-deoxy-L-galactose (L-fucose) to L-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on D-fucose afforded 6-deoxy-D-tagatose. Thus, the polylol dehydrogenase recognizes the D-galacto-configuration of both D-fucitol and L-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-D-tagatose was also synthesized from D-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-alpha-D-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive. (c) 2008 Elsevier Ltd. All rights reserved.