Glycolic Acid → Glyoxylic Acid
Reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N)CN.C(O)(=[O:14])C(C)C.[C:16]([O-:20])(=[O:19])[CH2:17][OH:18]>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:17]([OH:14])(=[O:18])[C:16]([OH:20])=[O:19]Participants
Conditions
- Temperature
- 5 °C
Procedure
A 300-mL EZE-Seal stirred autoclave reactor equipped with Dispersimax Impeller (Autoclave Engineers) was charged with 100 mL of a solution containing glycolic acid (0.750M), ethylenediamine (0.863M), isobutyric acid (0.100M, HPLC internal standard), and flavin mononucleotide (0.01 mM), at pH 9.2, and the solution cooled to 5° C. To the reactor was then added 30 g of E. coli transformant d01 (72 IU glycolate oxidase and 29,600 IU catalase), and the mixture stirred at 1000 rpm, which bubbled oxygen through the mixture via the action of the turbine impeller, and at 5° C. under 120 psig of oxygen. 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 23 h, the yields of glyoxylic acid, oxalic acid, and formic acid were 74.4%, 1.1%, and 5.6%, respectively, with 6.3% glycolic acid remaining. The recovered activities of microbial glycolate oxidase and catalase were 30% and 199% of their initial values, respectively.
Workup
- customA 300-mL EZE-Seal stirred autoclave reactor equipped with Dispersimax Impeller (Autoclave Engineers)
- additionTo the reactor was then added 30 g of E
- custombubbled oxygen through the mixture via the action of the turbine impeller
- customat 5° C.
- filtrationfiltering the aliquot
- filtrationFilter Unit
Sources & evidence
- ORD record
- ord-5b52983de8f74af4a26cfcfc3bee29b6
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05834262
Reaction notes
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