Glycolic Acid → Formate

HRID 1736283Notes

Reaction equation

HRID 1736283 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].NCP(=O)(O)O.[C:12]([OH:17])(=[O:16])C(C)C.[OH-].[Na+].[C:20]([O-:24])(=[O:23])[CH2:21][OH:22].CCC(C[O:31]C(C(N(CC[NH+](C)C)C)=O)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[Cl-]>>[C:1]([O-:5])(=[O:4])[CH:2]=[O:3].[CH:12]([O-:17])=[O:16].[C:21]([O-:31])(=[O:22])[C:20]([O-:24])=[O:23]

Participants

9

Reactant 6

HCID 757Glycolic AcidHCID 6590Isobutyric AcidHCID 14017(Aminomethyl)phosphonic acidHCID 14798Sodium Hydroxide2×HCID 19153X 100HCID 5460308Hydroxyacetate

Product 3

HCID 283FormateHCID 71081OxalateHCID 3614358Npc324351

Conditions

Temperature
5 °C

Procedure

Into a 3 oz. Fischer-Porter glass aerosol reaction vessel was placed a magnetic stirring bar and 10 mL of an aqueous 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 vessel was then added 0.47 g of Hansenula polymorpha transformant GO1 (10 IU glycolate oxidase and 22,100 IU catalase) which had been permeabilized by treatment with 0.1% "TRITON" X-100/1 freeze-thaw, and 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 the reaction vessel was sealed and the reaction mixture was cooled to 5° C. The vessel was flushed with oxygen by pressurizing to 70 psig and venting to atmospheric pressure five times with stirring, then the vessel was pressurized to 70 psig of oxygen and the mixture stirred at 5° C. Aliquots (0.10 mL) were removed by syringe through a sampling port (without loss of pressure in the vessel) at regular intervals for analysis by HPLC to monitor the progress of the reaction. After 16 hours, the HPLC yields of glyoxylate, formate, and oxalate were 90.1%, 1.3%, and 5.9%, respectively, and 3.0% glycolate remained. The remaining glycolate oxidase activity and total catalase activity were 86% and 136%, respectively, of their initial values.

Workup

  1. customFischer-Porter glass aerosol reaction vessel
  2. customthe reaction vessel was sealed
  3. temperaturethe reaction mixture was cooled to 5° C
  4. customThe vessel was flushed with oxygen
  5. stirringthe mixture stirred at 5° C
  6. customAliquots (0.10 mL) were removed by syringe through a sampling port (without loss of pressure in the vessel) at regular intervals for analysis by HPLC
  7. customthe progress of the reaction

Sources & evidence

ORD record
ord-7b4b3d1fee2e42dbaf057914c0613ff5
Source dataset
uspto-grants-1996_07
Patent number
US05541094

Reaction notes

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