NADP nicotinamide-adenine-dinucleotide phosphate → 2-Chloro-1-(3-chloro-phenyl)-ethanol
Reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.[Cl:61][CH2:62][C:63]([C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([Cl:71])[CH:66]=1)=[O:64].[OH-].[Na+]>>[Cl:61][CH2:62][CH:63]([C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([Cl:71])[CH:66]=1)[OH:64]Participants
Conditions
- Temperature
- 30 °C
Procedure
The culture of the recombinant Escherichia coli HB101 (pNTRGG1) as obtained in Example 9 was subjected to ultrasonic cell disruption using SONIFIRE 250 (product of BRANSON). To 20 ml of this cell disruption fluid, there were added 3 g of glucose, 2 mg of NADP and 2 g of 2-chloro-1-(3′-chlorophenyl)ethanone. This reaction mixture was stirred at 30° C. for 24 hours while adjusting the pH to 6.5 by dropwise addition of 5 M sodium hydroxide. After completion of the reaction, this reaction mixture was extracted with toluene, the solvent was then removed, and the extract was analyzed in the same manner as in Example 10. 2-Chloro-1-(3′-chlorophenyl)ethanol was obtained in 93% yield. The 2-chloro-1-(3′-chlorophenyl)ethanol formed on that occasion was the R form with an optical purity of 99.9% ee.
Workup
- customThe culture of the recombinant Escherichia coli HB101 (pNTRGG1) as obtained in Example 9
- customAfter completion of the reaction
- extractionthis reaction mixture was extracted with toluene
- customthe solvent was then removed
Sources & evidence
- ORD record
- ord-54deea640049453a98485207026a3751
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332312B2
Reaction notes
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