Synthesis of Enantiomerically Pure Ring-Substituted l-Pyridylalanines by Biocatalytic Hydroamination

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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.

Bibliographical metadata

Original languageEnglish
JournalOrganic Letters
Early online date21 Oct 2016
Publication statusPublished - 2016