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Asymmetric Synthesis of Optically Pure Pharmacologically Relevant Amines Employing ω‐Transaminases
Author(s) -
Koszelewski Dominik,
Lavandera Iván,
Clay Dorina,
Rozzell David,
Kroutil Wolfgang
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800496
Subject(s) - chemistry , stereoselectivity , amination , enantiomer , substrate (aquarium) , reductive amination , transaminase , enantiomeric excess , stereochemistry , enantioselective synthesis , solvent , medicinal chemistry , organic chemistry , catalysis , enzyme , oceanography , geology
Various ω‐transaminases were tested for the synthesis of enantiomerically pure amines from the corresponding ketones employing D ‐ or L ‐alanine as amino donor and lactate dehydrogenase to remove the side‐product pyruvate to shift the unfavourable reaction equilibrium to the product side. Both enantiomers, ( R )‐ and ( S )‐amines, could be prepared with up to 99% ee and >99% conversions within 24 h at 50 mM substrate concentration. The activity and stereoselectivity of the amination reaction depended on the ω‐transaminase and substrate employed; furthermore the co‐solvent significantly influenced both the stereoselectivity and activity of the transaminases. Best results were obtained by employing ATA‐117 to obtain the ( R )‐enantiomer and ATA‐113 or ATA‐103 to access the ( S )‐enantiomer with 15% v v −1 DMSO.