Reaction #1178407

Reaction equation

glucose

glucose

acetophenone

sodium hydroxide

→

(S)-phenylethanol

Yield 96.4%

Conditions

Workup

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

Procedure

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