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

Journal article

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-α-d-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive. © 2008 Elsevier Ltd. All rights reserved.

Authors: Yoshihara, A; Haraguchi, S; Gullapalli, P; Rao, D; Morimoto, K

• Publication status: Published
• Journal: TETRAHEDRON-ASYMMETRY
• Volume: 19
• Issue: 6
• Pages: 739-745
• Publication date: 2008-04-03
• DOI: 10.1016/j.tetasy.2008.02.013
• EISSN: 1362-511X
• ISSN: 0957-4166
• Language: English