Glycolic Acid → Formate
Reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(O)C(N)(CO)C[OH:9].[C:14]([OH:18])(=[O:17])CC.[C:19]([O-:23])(=[O:22])[CH2:20][OH:21].[OH-].[Na+]>>[C:1]([O-:5])(=[O:4])[CH:2]=[O:3].[C:20]([O-:9])(=[O:21])[C:19]([O-:23])=[O:22].[CH:14]([O-:18])=[O:17]Participants
Conditions
- Temperature
- 30 °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 (250 mM), tris(hydroxymethyl)aminomethane (TRIS, 330 mM), FMN (0.02 mM), propionic acid (HPLC internal standard, 75 mM), glycolate oxidase (from spinach; 0.25 IU/mL), and catalase (from Aspergillus niger; 1400 IU/mL). The final pH of this solution was adjusted to 8.3 with 5% NaOH. The reaction vessel was sealed and the reaction mixture was cooled to 30° C., then the vessel was flushed with oxygen by pressurizing to 15 psig and venting to atmospheric pressure five times with stirring. The vessel was then pressurized to 15 psi of oxygen with stirring Aliquots (0.10 mL) were removed 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 30 hours, the HPLC yields of glyoxylate, oxalate, and formate were 89.5%, 3.3%, and 2.8%, respectively, and no glycolate remained. The remaining activity of glycolate oxidase and catalase were 52% and 60% 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
- customwere removed through a sampling port (without loss of pressure in the vessel) at regular intervals for analysis by HPLC
- customthe progress of the reaction
Sources & evidence
- ORD record
- ord-af28ecc19db3402a989e6388bbd376e4
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05221621
Reaction notes
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