Ethylenediaminetetraacetic Acid → Glucuronic acid 1-phosphate

HRID 1059063Notes

Reaction equation

HRID 1059063 reaction equation
[P:1]([O-:16])([O-:15])([O:3][C@H:4]1[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6])=[O:2].[K+].[Br-].CC1(C)N([O])C(C)(C)CCC1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=[O:35].C(OO)(=O)C.[OH-].[K+]>O>[P:1]([O:3][C@H:4]1[O:12][C@H:11]([C:13]([OH:35])=[O:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6])([OH:16])([OH:15])=[O:2]

Participants

8

Reactant 6

HCID 6049Ethylenediaminetetraacetic AcidHCID 6585Peracetic AcidHCID 14797Potassium HydroxideHCID 253877Potassium BromideHCID 2724126TempoHCID 7091266α-D-Glucopyranose, 1-(dihydrogen phosphate), ion(2-)

Product 1

HCID 439432Glucuronic acid 1-phosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. customThe product crystallized from the mixture
  2. additionafter addition of MeOH

Sources & evidence

ORD record
ord-6c931bb531b9445f914ffa26e8bd615e
Source dataset
uspto-grants-2003_02
Patent number
US06518419B1

Reaction notes

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