Glycolic Acid → Glyoxylic Acid
Reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N)CN.C(O)(=[O:13])CC.[C:15]([O-:19])(=[O:18])[CH2:16][OH:17].O=O>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:16]([OH:13])(=[O:17])[C:15]([OH:19])=[O:18]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 (0.75M), ethylenediamine (0.86M, pH 9.2), propionic acid (0.075M, HPLC internal standard), and flavin mononucleotide (0.01 mM), and the solution cooled to 5° C. To the reactor was then added 32 g of frozen (-80° C.) Aspergillus nidulans FT17SYG/OL (28.2 IU glycolate oxidase and 157,000 IU catalase), and the cells were allowed to thaw at 15° C. The resulting mixture was stirred at 400 rpm and 5° C. under 70 psig (483 kPa) of oxygen, while bubbling oxygen through the mixture at 30 mL/min. The reaction was monitored by taking a 100 μL aliquot of the reaction mixture at regular intervals, mixing the aliquot with 300 μL of 0.1N sulfuric acid to quench the reaction, filtering the aliquot and analyzing by HPLC. After 21 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 88.2%, 0%, and 0%, respectively, with 10.0% recovery of glycolic acid. The final activities of glycolate oxidase and catalase were 0% and 75% of their initial values.
Workup
- additionTo the reactor was then added 32 g
- temperatureof frozen (-80° C.)
- customthaw at 15° C
- customwhile bubbling oxygen through the mixture at 30 mL/min
- additionmixing the aliquot with 300 μL of 0.1N sulfuric acid
- customto quench
- customthe reaction
- filtrationfiltering the aliquot and analyzing by HPLC
Sources & evidence
- ORD record
- ord-1e606fa70b9b400f81ee8be9f6625f8a
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05834262
Reaction notes
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