HCID 86589658, compound → Phosphoglycolic Acid

HRID 967691Notes

Reaction equation

HRID 967691 reaction equation
[P:1]([O:5][CH2:6][C:7]([O-:9])=[O:8])([OH:4])([OH:3])=[O:2].[CH:10]1([NH3+])[CH2:15]CCC[CH2:11]1.C1([NH3+])CCCCC1.C1([NH3+])CCCCC1.P([O:35][CH2:36]C([O-])=O)(O)(O)=O.P([O:44][CH2:45]C([O-])=O)(O)(O)=O>CO>[P:1]([O:5][CH2:6][C:7]([OH:9])=[O:8])([OH:4])([OH:3])=[O:2].[CH3:36][O:35][C:10]([O:44][CH3:45])([CH3:15])[CH3:11]

Participants

4

Reactant 1

HCID 86589658HCID 86589658, compound

Product 2

HCID 529Phosphoglycolic AcidHCID 64952,2-Dimethoxypropane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

PGH is synthesized from tri(monocyclohexylammonium) 2-phosphoglycolate (Sigma-Aldrich Chemie GmBH, Germany), which is first converted into the free acid form using Dowex 50W-H+. Treatment of the 2-phosphoglycolic acid with 2,2-dimethoxypropane in methanol yielded the methyl ester 2PG, which is converted to PGH (Collins, K. D. (1974) J. Biol. Chem. 249:136-142). Purification of PGH to homogeneity is done on a DEAE Sephadex A-25 column using a 0-0.4 M lithium chloride gradient. Two consecutive purification columns are needed to obtain a product free of 2PG. PGH is isolated from LiCl by precipitation with barium salts (Lewis, D. J. & Lowe, G., (1977) Eu.r.J. Biochem. October, 17;80(1):119-33). The purity of the barium salt of PGH was confirmed by P NMR and H NMR and mass spectrometry. PGH solutions are prepared as described (Lewis & Lowe, 1977), and the concentration of dissolved PGH is determined spectrophotometrically (Collins, 1974).

Sources & evidence

ORD record
ord-63a95a87266c4376be7cdd5ba8ad3540
Source dataset
uspto-grants-2005_10
Patent number
US06955890B2

Reaction notes

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