A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose-3-epimerase—a reagent that is both specific and general
✍ Scribed by Devendar Rao; Daniel Best; Akihide Yoshihara; Pushpakiran Gullapalli; Kenji Morimoto; Mark R. Wormald; Francis X. Wilson; Ken Izumori; George W.J. Fleet
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 414 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 b-pyranose form whereas both pyranoses of 5-deoxy-D-fructose [a:b. 22:78] are observed.