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

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 bot...

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Published inTetrahedron: asymmetry Vol. 19; no. 6; pp. 739 - 745
Main Authors Yoshihara, Akihide, Haraguchi, Satoshi, Gullapalli, Pushpakiran, Rao, Davendar, Morimoto, Kenji, Takata, Goro, Jones, Nigel, Jenkinson, Sarah F., Wormald, Mark R., Dwek, Raymond A., Fleet, George W.J., Izumori, Ken
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.04.2008
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
D-PSICOSE
D-TAGATOSE
D-TALITOL
D-GALACTITOL
RIBITOL
STRATEGY
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2008.02.013