Synthesis of (R)- or (S)-valinol using ω-transaminases in aqueous and organic media
Autor: | Christine S. Fuchs, Waander Riethorst, Robert C. Simon, Wolfgang Kroutil, Ferdinand Zepeck |
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Rok vydání: | 2014 |
Předmět: |
Methyl Ethers
Ketone Clinical Biochemistry Pharmaceutical Science Biochemistry Medicinal chemistry Reductive amination chemistry.chemical_compound Drug Discovery Organic chemistry Valinol Enantiomeric excess Molecular Biology Transaminases Amination chemistry.chemical_classification Alanine Aqueous solution Molecular Structure Organic Chemistry Water Stereoisomerism Valine chemistry Biocatalysis Molecular Medicine Amine gas treating |
Zdroj: | Bioorganicmedicinal chemistry. 22(20) |
ISSN: | 1464-3391 |
Popis: | Valinol is part of numerous pharmaceuticals and has various other important applications. Optically pure valinol (ee >99%) was prepared employing different ω-transaminases from the corresponding prochiral hydroxy ketone. By the choice of the enzyme the (R)- as well as the (S)-enantiomer were accessible. Reductive amination was performed in organic solvent (MTBE) using 2-propyl amine as amine donor whereas alanine was applied in or in aqueous medium. Transformations in phosphate buffer were successfully performed even at 200 mM substrate concentration (20.4 g/L) leading to 99% (R) and 94% (S) conversion with perfect optical purity (>99% ee). |
Databáze: | OpenAIRE |
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