Sulfuric Acid → HCID 54545516, compound

HRID 1647082Notes

Reaction equation

HRID 1647082 reaction equation
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.C(=O)([O-])[O-].[Ca+2].[O:29]=[C:30]([CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([O-:33])=[O:32].[K+].S(=O)(=O)(O)O>O>[OH:29][C@H:30]([CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([OH:33])=[O:32]

Participants

6

Conditions

Temperature
30 °C

Procedure

A medium comprising 2% glucose, 1% yeast extract, 1% peptone, 10 ppm MnSO4 and 1% calcium carbonate was used for lactic acid bacteria. A medium comprising 1% glucose, 0.5% yeast extract, 0.5% peptone, 0.5% meat extract and 0.5% NaCl (pH 7) was used for other bacteria. A medium comprising 2% glucose, 0.3% yeast extract, 0.5% peptone and 0.3% malt extract (pH 6) was used for yeasts. 100 ml of each medium was introduced into a 500-ml Erlenmeyer flask and sterilized. Then one platinum loopful of each strain listed in Table 1 was inoculated into the corresponding medium and subjected to rotary shaking culture for 48 hours. After completion of the culture, the cells were separated by centrifuging and washed with a physiological saline solution once to thereby give viable cells. 50 ml of distilled water was introduced into a 500-ml Erlenmeyer flask and the above-mentioned viable cells were suspended therein. After adding 5 g of sucrose and 0.5 g of calcium carbonate thereto, the mixture was shaken at 30° C. for 10 minutes. Then 0.5 g of potassium 2-keto-4-phenyl-3-butenoate was added thereto and the mixture was allowed to react under shaking at 30° C. for 40 hours. After the completion of the reaction, the pH value of the reaction mixture was adjusted to 1 or below with sulfuric acid. Then it was extracted with 100 mi of ethyl acetate and the solvent was removed from the extract. Then the amount and optical purity of the (R)-2-hydroxy-4-phenyl-3-butenoic acid thus formed were determined by high-performance liquid chromatography.

Workup

  1. extractionA medium comprising 2% glucose, 1% yeast extract
  2. extractionextract
  3. extraction0.5% peptone, 0.5% meat extract
  4. extractionextract
  5. extraction0.5% peptone and 0.3% malt extract (pH 6)
  6. addition100 ml of each medium was introduced into a 500-ml Erlenmeyer flask
  7. customAfter completion of the culture, the cells were separated by centrifuging
  8. washwashed with a physiological saline solution once
  9. customto thereby give viable cells
  10. customto react
  11. stirringunder shaking at 30° C. for 40 hours
  12. customAfter the completion of the reaction
  13. extractionThen it was extracted with 100 mi of ethyl acetate
  14. customthe solvent was removed from the extract

Sources & evidence

ORD record
ord-97644c7bf9074137975f23a173e564cb
Source dataset
uspto-grants-1995_07
Patent number
US05429935

Reaction notes

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