Glycolic Acid → Formate

Participants

Reaction Conditions

Reaction Steps

Into a 3 oz. Fischer-Porter glass aerosol reaction vessel was placed a magnetic stirring bar and 10 mL of an aqueous solution containing glycolic acid (0.50M), FMN (0.01 mM), isobutyric acid (HPLC internal standard, 0.10M), glycolate oxidase (from spinach, 1.0 IU/mL), and catalase (from Aspergillus niger, 14,000 IU/mL) at pH 8.5. The reaction vessel was sealed and the reaction mixture was cooled to 5° C., then the vessel was flushed with oxygen by pressurizing to 70 psig and venting to atmospheric pressure five times with stirring. The vessel was then pressurized to 70 psig of oxygen and the mixture stirred at 5° C. Aliquots (0.10 mL) were removed by syringe through a sampling port (without loss of pressure in the vessel) at regular intervals for analysis by HPLC to monitor the progress of the reaction. After 21 h, the HPLC yields of glyoxylate, formate, and oxalate were 81.7%, 1.2%, and 2.2%, respectively, and 7.5% glycolate remained. The remaining activity of glycolate oxidase and catalase were 19% and 77%, respectively, of their initial values. This reaction was then repeated with 0.50M glycolic acid and 0.25M, 0.375M, 0.40M, 0.50M, or 0.625M aminomethylphosphonic acid (AMPA) present, and the yields of reaction products and enzyme recoveries for these reactions are listed below:

Provenance & Evidence