title: Synthesis of (R)- or (S)-valinol using ω-transaminases in aqueous and organic media.
abstract: 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).
authors.affiliation: ACIB GmbH, Heinrichstraße 28, 8010 Graz, Austria.
authors.forename: Christine S
authors.initials: CS
authors.lastname: Fuchs
authors.affiliation: University of Graz, Institute of Chemistry, Organic- and Bioorganic Chemistry, NAWI Graz, 8010 Graz, Austria.
authors.forename: Robert C
authors.initials: RC
authors.lastname: Simon
authors.affiliation: Sandoz GmbH, Development Anti-Infectives, Biochemiestraße 10, 6250 Kundl/Tirol, Austria.
authors.forename: Waander
authors.initials: W
authors.lastname: Riethorst
authors.affiliation: Sandoz GmbH, Development Anti-Infectives, Biochemiestraße 10, 6250 Kundl/Tirol, Austria.
authors.forename: Ferdinand
authors.initials: F
authors.lastname: Zepeck
authors.affiliation: University of Graz, Institute of Chemistry, Organic- and Bioorganic Chemistry, NAWI Graz, 8010 Graz, Austria. Electronic address: wolfgang.kroutil@uni-graz.at.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Kroutil
mesh_terms: D000586:Amination; D008738:Methyl Ethers / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D013237:Stereoisomerism; D000637:Transaminases / Q000737:chemistry / Q000378:metabolism*; D014633:Valine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D014867:Water / Q000737:chemistry / Q000378:metabolism
chemical_list: D008738:Methyl Ethers; D014867:Water; C043243:methyl tert-butyl ether; C040994:valinol; D000637:Transaminases; D014633:Valine
keywords: Amino-alcohols; Biocatalysis; Reductive amination; Valinol; ω-Transaminases