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].O=O>>[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. To the reactor was then added 26 g of frozen (-80° C.) Aspergillus nidulans FT17SYCSL/OL (124 IU glycolate oxidase and 57,800 IU catalase) deposited with the Northern regional Research Laboratories on Sep. 24, 1992, under the terms of the Budapest Treaty and designated by the accession number NRRL 21000 and 1.4×106 units of Aspergillus niger soluble catalase (Sigma), the cells allowed to thaw at 5° C., and the pH of the resulting mixture re-adjusted to 8.3 with 50% NaOH. This mixture was stirred at 400 rpm and 5° C. under 120 psig of oxygen while bubbling oxygen through the mixture at 50 mL/min. The reaction was monitored by taking a 0.40 mL aliquot of the reaction mixture at regular intervals, filtering the aliquot using a Millipore "ULTRAFREE"-MC 10,000 NMWL Filter Unit, and analyzing the filtrate by HPLC. After 10 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 91%, 0%, and 7.9%, respectively, with 2.5% recovery of glycolic acid. The final activities of glycolate oxidase and Aspergillus niger catalase were 11% and 87% of their initial values.
Workup
- additionTo the reactor was then added 26 g
- temperatureof frozen (-80° C.)
- customthaw at 5° C.
- customwhile bubbling oxygen through the mixture at 50 mL/min
- filtrationfiltering the aliquot
- filtrationFilter Unit
Sources & evidence
- ORD record
- ord-cf1bdb48224c42fc885fb3a78e3e1a1c
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05541094
Reaction notes
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