ol6b02559_si_002.pdf (8.59 MB)
Synthesis of Enantiomerically Pure Ring-Substituted l‑Pyridylalanines by Biocatalytic Hydroamination
journal contribution
posted on 2016-10-21, 18:51 authored by Syed T. Ahmed, Fabio Parmeggiani, Nicholas J. Weise, Sabine
L. Flitsch, Nicholas J. TurnerCurrent
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.
History
Usage metrics
Categories
Keywords
deracemization cascadel-heteroarylalaninebiocatalystPureanaloguePALconversionl-pyridylalaninestrategyeemethodologyRing-Substitutednitrogen-containing heteroarylalaninesenantiopurityaldehydecomplementphenylalanine ammonia lyaseprotectionAnabaena variabilisBiocatalytic Hydroaminationmultistep synthesisyieldpurificationSynthesiEnantiomerically
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC