Glycolic Acid → Formate

HRID 1587653Notes

Reaction equation

HRID 1587653 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N)CN.[C:10]([O-:14])(=[O:13])[CH2:11][OH:12]>>[C:1]([O-:5])(=[O:4])[CH:2]=[O:3].[C:11]([O-:3])(=[O:12])[C:10]([O-:14])=[O:13].[CH:1]([O-:5])=[O:4]

Participants

6

Conditions

Temperature
15 °C

Procedure

Into a 3 ounce Fischer-Porter glass aerosol reaction vessel were placed a magnetic stirring bar and 10 mL of an aqueous solution containing glycolic acid (2000 mM), ethylenediamine (2100 mM), FMN (0.01 mM), glycolate oxidase (from spinach; 1.2 IU/mL), and catalase (from Aspergillus niger; 1400 IU/mL). The final pH of this solution was 9.0. 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 31 hours, no glycolate oxidase activity remained, so an additional 2.0 IU/mL of glycolate oxidase was added. After 143 hours, the HPLC yields of glyoxylate, oxalate, and formate were 96.8%, 2.2%, and 1.0%, respectively, and no glycolate remained. The remaining activity of glycolate oxidase (based on total) and catalase were 69% and 100% of their initial values, respectively.

Workup

  1. customInto a 3 ounce Fischer-Porter glass aerosol reaction vessel
  2. customThe reaction vessel was sealed
  3. customthe vessel was flushed with oxygen
  4. stirringthe mixture stirred
  5. custom0.10 mL aliquots were removed at regular intervals for analysis by HPLC
  6. customthe progress of the reaction
  7. waitAfter 143 hours

Sources & evidence

ORD record
ord-5279e0ac81bf43e28e87639e0c9b93c4
Source dataset
uspto-grants-1993_06
Patent number
US05219745

Reaction notes

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