Ethylenediaminetetraacetic Acid → Glucuronic acid 1-phosphate

Participants

Reaction Steps

1.97 g of α-Glc-1-P (2K+.C6H11O9P2−.2H2O, 5.5 mmol) was dissolved in 60 ml of water at room temperature. To this solution was added 210 mg KBr (1.76 mmol), 20 mg TEMPO (0.13 mmol), 10 mg EDTA, and 2.5 g KHCO3. Peracetic acid (10 ml, 1.69 mmol/ml) was added at a rate of 200 μl per 10 minutes. The pH was maintained at 8 by addition of 2M KOH using a pH-stat. After 16 h the reaction was complete. The product crystallized from the mixture after addition of MeOH to obtain α-D-glucopyranuronic acid 1-phosphate (3K+.C6H8O10P3−.5H2O, 1.90 g, 4.0 mmol, 73%), NMR (500 Mhz, D2O, in ppm): 1H δ 3,32 (dd, H-4J3,4=9.5 Hz, J4,5=9.9 Hz), 3.35 (m, H-2, JP,H2=1.8 Hz, J1,2=3.4 Hz, J2,3=9.5 Hz), 3.62 (dd, H-3, J2,3=9,5 Hz, J3,4 =9.5 Hz)), 3.99 (d, H-5, J4,5=9.9 Hz,), 5.30 (dd, H-1, JP,H1=7.3 Hz, J1,2=3.4 Hz), 13C δ71.4 (C-2), 71.5 (C-3,C-4), 72.4 (C-5), 93.0 (C-1), 176.6 (C-6).

Provenance & Evidence