Glycolic Acid → Glyoxylic Acid

HRID 1736282Notes

Reaction equation

HRID 1736282 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].NCP(=O)(O)[OH:9].[OH-].[Na+].[C:14]([O-:18])(=[O:17])[CH2:15][OH:16]>>[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:15]([OH:9])(=[O:16])[C:14]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 757Glycolic AcidHCID 14017(Aminomethyl)phosphonic acidHCID 14798Sodium HydroxideHCID 5460308Hydroxyacetate

Product 2

HCID 760Glyoxylic AcidHCID 971Oxalic Acid

Conditions

Temperature
-80 °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), flavin mononucleotide (0.01 mM), and no added HPLC internal standard (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 4×100 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 resulting mixture was stirred at 400 rpm and 5° C. under 120 psig of oxygen while bubbling oxygen through the mixture at 50 mL/min. After 11 hours, the yields of glyoxylic acid, oxalic acid, and formic acid were 89%, 4.5%, and 2.0%, respectively, with complete conversion of glycolic acid.

Workup

  1. customthaw at 5° C.
  2. washwashed with 4×100 mL of KH2PO4 (50 mM, pH 7.0)/FMN (0.01 mM) buffer at 5° C.
  3. additionthe washed cells added to the reactor with 1.4×106 units of Aspergillus niger soluble catalase (Sigma)
  4. customwhile bubbling oxygen through the mixture at 50 mL/min

Sources & evidence

ORD record
ord-0129b37e4b6e4917a1b7439a39a1b246
Source dataset
uspto-grants-1996_07
Patent number
US05541094

Reaction notes

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