Réaction #1178407

Équation de réaction

glucose

glucose

acetophenone

sodium hydroxide

→

(S)-phenylethanol

Rendement 96.4%

Conditions de réaction

Traitement

1. 1
   ExtractionThus, 100 mL of the cell-free extract
2. 2
   Autrewas produced
3. 3
   workup.ADDITIONwas added dropwise to the mixture
4. 4
   AutreAfter the reaction
5. 5
   Extractionthe reaction mixture was extracted with toluene
6. 6
   Séchagewas dried over anhydrous sodium sulfate
7. 7
   AutreRemoval of sodium sulfate, and evaporation of organic solvents from the organic layer

Mode opératoire

coli HB101 (pNCM) was cultivated in a similar manner to Example 9, and then cells were disrupted with an ultrasonic homogenizer. Thus, 100 mL of the cell-free extract was produced. In a 100-mL portion of this cell-free extract, 700 U of a glucose dehydrogenase (Trade name: GLUCDH “Amano” II, a product of Amano Enzyme Inc.), 17 g of glucose, 3 mg of NAD+, and 10 g of acetophenone were added, and the mixture was stirred at 30° C. for 20 hours while controlling the pH of the reaction mixture to 6.5 with 5 N aqueous sodium hydroxide, which was added dropwise to the mixture. After the reaction, the reaction mixture was extracted with toluene, and combined organic layer was dried over anhydrous sodium sulfate. Removal of sodium sulfate, and evaporation of organic solvents from the organic layer yielded 9.8 g of (S)-phenylethanol. The product (S)-phenylethanol was analyzed in accordance with the [Analysis condition (1) for gas chromatography] as described above, and found that the optical purity of the product was 99.9% e.e. or higher.

Source