Urea → Malic Acid

HRID 1165116Notes

Reaction equation

HRID 1165116 reaction equation
[O:1]=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[C:13]([O-:20])(=[O:19])/[CH:14]=[CH:15]/[C:16]([O-:18])=[O:17].[Na+].[Na+].NC(N)=O.P([O-])(O)(O)=O.[K+]>P([O-])([O-])([O-])=O>[C:13]([OH:20])(=[O:19])[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[OH:1].[C:13]([OH:20])(=[O:19])/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 1176UreaHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516951Monobasic potassium phosphateHCID 6364607Disodium fumarate

Product 2

HCID 525Malic AcidHCID 444972Fumaric Acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Washed cells of Brevibacterium ammoniagenes (IAM 1645) deposited at and obtained from the Institute of Applied Microbiology, University of Tokyo, was prepared by aerobically culturing the strain in a medium (pH 7.2) comprising glucose 2%, sodium fumarate 0.5%, urea 0.2%, monopotassium dihydrogen phosphate 0.2%, magnesium sulfate·7 hydrate 0.05% and corn steep liquor 1%. The cells were dispersed in 0.05 M phosphate buffer (pH 7.7) at a dark place to prepare a suspension of cells having a concentration of 30.0 OD630 μm. The bacterial liquor was divided into two portions. One portion thereof was allowed to stand at 30° C. for 1 hour at a distance of 20 cm apart from a 150 W "Cool Beam" light (supplied from Tokyo Shibaura Denki K. K., Japan) at light energy of 7×102 μE/g cells·second (light-standing). The other portion thereof was allowed to stand at 30° C. for 1 hour at a dark place (dark-standing). By using these bacterial liquor in the following formulations, malic acid was produced from fumaric acid. The reaction velocity was studied in comparison with the amounts of malic acid thus produced.

Workup

  1. washWashed cells of Brevibacterium ammoniagenes (IAM 1645)
  2. customobtained from the Institute of Applied Microbiology, University of Tokyo
  3. customwas prepared
  4. customto prepare
  5. additiona suspension of cells
  6. temperatureCool Beam" light (supplied from Tokyo Shibaura Denki K. K., Japan) at light energy of 7×102 μE/g cells·second (light-standing)
  7. waitto stand at 30° C. for 1 hour at a dark place (dark-standing)

Sources & evidence

ORD record
ord-af6f9a5bd76046ceba5ae4edaa373154
Source dataset
uspto-grants-1990_03
Patent number
US04908313

Reaction notes

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