Reaction #1178408

Reaction equation

sodium hydroxide

glucose

acetophenone

→

(S)-phenylethanol

Yield 97.4%

Conditions

Workup

1. 1
   OtherCulture fluid was obtained
2. 2
   workup.ADDITIONwas added dropwise to the mixture
3. 3
   OtherAfter the reaction
4. 4
   Extractionthe reaction mixture was extracted with toluene
5. 5
   Dryingwas dried over anhydrous sodium sulfate
6. 6
   OtherRemoval of sodium sulfate, and evaporation of organic solvents from the organic layer under reduced pressure

Procedure

Culture fluid was obtained by cultivating E. coli HB101 (pNCMG) in a similar manner to Example 9. In a 100-mL portion of the culture fluid, 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 under reduced pressure yielded 9.9 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