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Enzymatic Preparation of an (S)-Amino Acid from a Racemic Amino Acid
- Source :
- Organic Process Research & Development. 15:241-248
- Publication Year :
- 2010
- Publisher :
- American Chemical Society (ACS), 2010.
-
Abstract
- The (S)-amino acid, (S)-2-amino-3-(6-o-tolylpyridin-3-yl)propanoic acid (3), is a key intermediate needed for synthesis of an antidiabetic drug candidate. Three enzymatic routes to 3 were explored. (S)-Amino acid 3 could be prepared in 73% isolated yield with 99.9% ee from racemic amino acid 1 using (R)-amino acid oxidase from Trigonopsis variabilis expressed in Escherichia coli in combination with an (S)-aminotransferase using (S)-aspartate as amino donor. The (S)-aminotransferase was purified from a soil organism identified as Burkholderia sp. and cloned and expressed in E. coli. (S)-Amino acid 3 with 100% ee was also prepared in 68% solution yield and 54% isolated yield from 1 using recombinant (R)-amino acid oxidase from T. variabilis and an (S)-amino acid dehydrogenase from Sporosarcina ureae. The cofactor NADH required for the reductive amination reaction was regenerated using formate and formate dehydrogenase. The chemoenzymatic dynamic resolution of 1 by (R)-selective oxidation with Celite-immobil...
- Subjects :
- chemistry.chemical_classification
biology
Stereochemistry
Organic Chemistry
Dehydrogenase
Formate dehydrogenase
biology.organism_classification
Reductive amination
Cofactor
Amino acid
chemistry.chemical_compound
Propanoic acid
chemistry
biology.protein
Formate
Physical and Theoretical Chemistry
Sporosarcina ureae
Subjects
Details
- ISSN :
- 1520586X and 10836160
- Volume :
- 15
- Database :
- OpenAIRE
- Journal :
- Organic Process Research & Development
- Accession number :
- edsair.doi...........3f8524bf49371550bc408822a7fa0a4c