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Asymmetric acyloin condensation catalyzed by phenylpyruvate decarboxylase
- Source :
- Tetrahedron: Asymmetry. 10:4667-4675
- Publication Year :
- 1999
- Publisher :
- Elsevier BV, 1999.
-
Abstract
- Cells obtained from growth of Achromobacter eurydice , Pseudomonas aromatica and Pseudomonas putida on l -phenylalanine containing medium catalyzed the enzymatic acyloin condensation of phenylpyruvic acid 1 and acetaldehyde 2 by phenylpyruvate decarboxylase to produce 3-hydroxy-1-phenyl-2-butanone 3 . The acyloin condensation by Achromobacter eurydice and P. aromatica was stereoselective, providing the 3 R enantiomer 3a with enantiomeric excess (ee) of 95% and 84%, respectively. A partially purified enzyme was prepared from the cell free extract of Achromobacter eurydice. The acyloin product 3a was obtained in 45% yield with an ee of 91% by using this partially purified preparation of phenylpyruvate decarboxylase.
- Subjects :
- Achromobacter
biology
Phenylpyruvate decarboxylase
Acyloin condensation
Organic Chemistry
Acetaldehyde
Phenylpyruvic acid
biology.organism_classification
Catalysis
Pseudomonas putida
Inorganic Chemistry
chemistry.chemical_compound
chemistry
Organic chemistry
Physical and Theoretical Chemistry
Enantiomer
Enantiomeric excess
Subjects
Details
- ISSN :
- 09574166
- Volume :
- 10
- Database :
- OpenAIRE
- Journal :
- Tetrahedron: Asymmetry
- Accession number :
- edsair.doi...........96424e83ca8df23dd42f1b4e11084167