Oxygen → Acetate

HRID 658967Notes

Reaction equation

HRID 658967 reaction equation
O=O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH2:15]1[C@@H:20]([OH:21])[C@@H:19]([OH:22])[C@H:18]([OH:23])[CH2:17][C@@:16]1([C:25]([OH:27])=[O:26])[OH:24].C1[C@:34](O)([C:35]([OH:37])=[O:36])CC(=O)[C@@H](O)[C@@H]1O>>[CH2:15]1[C@@H:20]([OH:21])[C@@H:19]([OH:22])[C@H:18]([OH:23])[CH2:17][C@@:16]1([C:25]([OH:27])=[O:26])[OH:24].[C:35]([O-:37])(=[O:36])[CH3:34]

Participants

6

Reactant 4

HCID 977OxygenHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 4393513-Dehydroquinic Acid2×HCID 178524980HCID 178524980, compound3×

Product 2

HCID 175AcetateHCID 178524980HCID 178524980, compound

Procedure

QP1.1/pKD12.112 was cultured for 60 h under fed-batch fermentor conditions at 37° C., pH 7.0, dissolved oxygen at 10% of saturation and an initial glucose concentration of 23 g/L. Extracellular accumulation of quinic acid began in early to mid log phase of microbial growth as represented by the open boxes in FIG. 2. The dry cell weight is represented by the solid line and closed circles. 3-Dehydroquinate was efficiently converted to quinic acid as there was never a build-up of the intermediate (solid bars in FIG. 2). After 60 hours of cultivation with Kc=0.1, E. coli QP1.1/pKD12.112 synthesized 60 g/L of quinic acid in 23% yield along with only 2.6 g of 3-dehydroquinate. Quinic acid was isolated from the fermentation broth by ion-exchange chromatography on AG1-x8 (acetate form) and Dowex 50 (H+ form) columns. Purified quinic acid was obtained by further recrystallization.

Workup

  1. customclosed circles
  2. waitAfter 60 hours of cultivation with Kc=0.1, E

Sources & evidence

ORD record
ord-c0ed24d9bb214b79afc34de9b2c740f5
Source dataset
uspto-grants-2011_12
Patent number
US08080397B2

Reaction notes

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