A concise approach to the synthesis of all twelve 5-deoxyhexoses: D-tagatose-3-epimerase-a reagent that is both specific and general

Journal article

2-Deoxy-d-glucitol and 2-deoxy-d-allitol, both prepared as crystalline polyols from d-erythronolactone, are oxidized by Gluconobacter thailandicus NBRC 3254 to 5-deoxy-d-threo-hexulose [5-deoxy-d-fructose = 5-deoxy-l-sorbose] and 5-deoxy-d-erythro-hexulose [5-deoxy-l-psicose = 5-deoxy-d-tagatose], respectively. d-Tagatose-3-epimerase (DTE) equilibrates 5-deoxy-d-fructose to 5-deoxy-d-psicose and 5-deoxy-l-psicose to 5-deoxy-l-fructose, providing substrates for the preparation of all eight d- and l-5-deoxy aldohexoses by aldose isomerases. This combination of chemical and biotechnological methods allows a concise approach to the synthesis of all twelve 5-deoxy hexoses and further demonstrates the range of deoxy sugar substrates on which DTE is active. NMR studies show that 5-deoxy-d-fructose exists solely as the β-pyranose form whereas both pyranoses of 5-deoxy-d-fructose [α:β. 22:78] are observed. [For the sake of clarity, all ketoses in this Letter are shown in blue, alditols in red and aldoses in purple.]. © 2009 Elsevier Ltd. All rights reserved.

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

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 50
• Issue: 26
• Pages: 3559-3563
• Publication date: 2009-07-01
• DOI: 10.1016/j.tetlet.2009.03.061
• ISSN: 0040-4039
• Language: English