An inositol → 2,4,6/3,5-Pentahydroxycyclohexanone

Participants

Reaction Steps

Angyal, S. J. et al. Carbohydr. Res. 76:121 (1979); Posternak, T., Biochem. Prep. 2:57 (1952). A solution containing sorbitol (1.0 g) and yeast extract (0.05 g) in 10 mL distilled, deionized water was autoclaved for 25 min and cooled to room temperature. After inoculation with Gluconobacter oxydans ATCC 621 the culture was incubated in an orbital shaker at 200 rpm for 24, h at 30° C. This G. oxydans culture was subsequently added to a second sterile solution containing myo-inositol (12.0 g, 66.7 mmol), D-sorbitol (0.4 g), and yeast extract (2.0 g) in 400 mL distilled, deionized water. After incubation in an orbital shaker at 200 rpm for 48 h at 30° C., cells were removed by centrifugation. The resulting culture supernatant was concentrated to 75 mL, MeOH (400 mL) added, and the solution maintained at −20° C. for 12 h. Precipitate which formed was filtered, washed with MeOH, and dried to afford myo-2-inosose as a white powder (8.17 g, 69%). A second crop of myo-2-inosose (3.09 g, 26%) was obtained after maintaining the filtrate at −20° C. for an additional 12 h. mp 188-192° C. 1H NMR (D2O): δ4.25 (d,J=10 Hz, 2 H), 3.66 (dd, J=9, 9 Hz), 3.26 (m, 2 H). 13C NMR (D2O): δ206.0, 94.3, 76.2, 74.5, 74.1, 74.0, 73.3, 73.2.

Provenance & Evidence