Glycolic Acid → Glyoxylic Acid
Reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].NCP(=O)(O)O.C(O)(=[O:16])C(C)C.[OH-].[Na+].[C:20]([O-:24])(=[O:23])[CH2:21][OH:22]>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:21]([OH:16])(=[O:22])[C:20]([OH:24])=[O:23]Participants
Conditions
- Temperature
- 5 °C
Procedure
A 300-mL EZE-Seal stirred autoclave reactor (Autoclave Engineers) was charged with 100 mL of a solution containing glycolic acid (0.500M), aminomethylphosphonic acid (0.375M), isobutyric acid (0.100M, HPLC internal standard), and flavin mononucleotide (0.01 mM) at pH 8.3 (adjusted with 50% NaOH), and the solution cooled to 5° C. Frozen (-80° C.) Aspergillus nidulans FT17SYCSL/OL (26 g, 124 IU glycolate oxidase and 57,800 IU catalase) were allowed to thaw at 5° C., then washed with 2×100 mL of KH2PO4 (50 mM, pH 7.0)/FMN (0.01 mM) buffer at 5° C. and the washed cells added to the reactor with 1.4×106 units of Aspergillus niger soluble catalase (Sigma). The pH of the resulting mixture was re-adjusted to 8.3 with 50% NaOH, then stirred at 400 rpm and 5° C. under 120 psig of oxygen while bubbling oxygen through the mixture at 50 mL/min. After 11.5 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 94%, 3.5%, and 2.7%, respectively, with 1.3% recovery of glycolic acid. The final activities of glycolate oxidase and Aspergillus niger catalase were 7% and 77% of their initial values.
Workup
- temperatureFrozen (-80° C.)
- customthaw at 5° C.
- washwashed with 2×100 mL of KH2PO4 (50 mM, pH 7.0)/FMN (0.01 mM) buffer at 5° C.
- additionthe washed cells added to the reactor with 1.4×106 units of Aspergillus niger soluble catalase (Sigma)
- customwhile bubbling oxygen through the mixture at 50 mL/min
Sources & evidence
- ORD record
- ord-a4fdfcd2aa7846069142450070527ade
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05541094
Reaction notes
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