NADP nicotinamide-adenine-dinucleotide phosphate → Butanoic acid, 4-chloro-3-hydroxy-, ethyl ester
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.[OH-].[Na+].[Cl:63][CH2:64][C:65](=[O:72])[CH2:66][C:67]([O:69][CH2:70][CH3:71])=[O:68]>>[Cl:63][CH2:64][CH:65]([OH:72])[CH2:66][C:67]([O:69][CH2:70][CH3:71])=[O:68]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 4 g of glucose and 3 mg of NADP. While stirring this reaction mixture at 30° C. and adjusting the pH to 6.5 by dropwise addition of 5 M sodium hydroxide, a total of 2 g of ethyl 4-chloroacetoacetate was added to the mixture continuously at a rate of 0.2 g per hour. After completion of the addition, the reaction was further allowed to proceed for 12 hours. After completion of the reaction, this reaction mixture was extracted with ethyl acetate, the solvent was then removed, and the extract was analyzed. Ethyl 4-chloro-3-hydroxybutyrate was obtained in 98% yield. The ethyl 4-chloro-3-hydroxybutyrate formed on that occasion was the R form with an optical purity of 99% ee or more.
Workup
- customThe culture of the recombinant Escherichia coli HB101 (pNTRGG1) as obtained in Example 9
- additionAfter completion of the addition
- customAfter completion of the reaction
- extractionthis reaction mixture was extracted with ethyl acetate
- customthe solvent was then removed
Sources & evidence
- ORD record
- ord-efa5ffdb4e7845fb912a077d7af94ce1
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332312B2
Reaction notes
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