Glycolic Acid → Formate
Reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N)CN.[C:10]([OH:14])(=[O:13])CC.[C:15]([O-:19])(=[O:18])[CH2:16][OH:17]>>[C:1]([O-:5])(=[O:4])[CH:2]=[O:3].[C:16]([O-:13])(=[O:17])[C:15]([O-:19])=[O:18].[CH:10]([O-:14])=[O:13]Participants
Conditions
- Temperature
- 15 °C
Procedure
Into a 3 ounce Fischer-Porter glass aerosol reaction vessel were placed a magnetic stirring bar and 50 mL of an aqueous solution containing glycolic acid (750 mM), ethylenediamine (862 mM), FMN (0.1 mM), propionic acid (HPLC internal standard, 75 mM), glycolate oxidase (from spinach; 1.0 IU/mL), and catalase (from Aspergillus niger; 1400 IU/mL). The final pH of this solution was 8.9. The reaction vessel was sealed and the reaction mixture was cooled to 15° 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 psi of oxygen and the mixture stirred, and 0.10 mL aliquots were removed at regular intervals for analysis by HPLC to monitor the progress of the reaction. After 90 hours, the HPLC yields of glyoxylate, oxalate, and formate were 99.8%, 0.2%, and 0%, respectively, and no glycolate remained. The remaining activity of glycolate oxidase and catalase were 34% and 88% of their initial values, respectively.
Workup
- customInto a 3 ounce Fischer-Porter glass aerosol reaction vessel
- customThe reaction vessel was sealed
- customthe vessel was flushed with oxygen
- stirringthe mixture stirred
- custom0.10 mL aliquots were removed at regular intervals for analysis by HPLC
- customthe progress of the reaction
Sources & evidence
- ORD record
- ord-0cb38f2269de4b2b84372b5b96813ea2
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05219745
Reaction notes
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