title: Synthesis of Enantiomerically Pure Ring-Substituted l-Pyridylalanines by Biocatalytic Hydroamination.
abstract: Current routes to nitrogen-containing heteroarylalanines involve complex multistep synthesis and are often reliant on protection/deprotection steps and wasteful chromatographic purifications. In order to complement existing methodologies, a convenient telescopic strategy was developed for the synthesis of l-pyridylalanine analogues (12 examples) and other l-heteroarylalanines (5 examples) starting from the corresponding aldehydes. A phenylalanine ammonia lyase (PAL) from Anabaena variabilis was used as the biocatalyst to give conversions ranging between 88 and 95%, isolated yields of 32-60%, and perfect enantiopurity (>99% ee) by employing an additional deracemization cascade where necessary.
authors: School of Chemistry, The University of Manchester, Manchester Institute of Biotechnology , 131 Princess Street, M1 7DN Manchester, United Kingdom.
authors: Syed T
authors: ST
authors: Ahmed
authors: School of Chemistry, The University of Manchester, Manchester Institute of Biotechnology , 131 Princess Street, M1 7DN Manchester, United Kingdom.
authors: Fabio
authors: F
authors: Parmeggiani
authors: School of Chemistry, The University of Manchester, Manchester Institute of Biotechnology , 131 Princess Street, M1 7DN Manchester, United Kingdom.
authors: Nicholas J
authors: NJ
authors: Weise
authors: School of Chemistry, The University of Manchester, Manchester Institute of Biotechnology , 131 Princess Street, M1 7DN Manchester, United Kingdom.
authors: Sabine L
authors: SL
authors: Flitsch
authors: School of Chemistry, The University of Manchester, Manchester Institute of Biotechnology , 131 Princess Street, M1 7DN Manchester, United Kingdom.
authors: Nicholas J
authors: NJ
authors: Turner