Synthesis of Enantiomerically Pure Ring-Substituted l‑Pyridylalanines by Biocatalytic Hydroamination
Version 2 2016-10-31, 16:51
Version 1 2016-10-21, 18:51
Posted on 2016-10-21 - 00:00
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.
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Ahmed, Syed T.; Parmeggiani, Fabio; Weise, Nicholas J.; Flitsch, Sabine
L.; Turner, Nicholas J. (2016). Synthesis of Enantiomerically Pure Ring-Substituted l‑Pyridylalanines by Biocatalytic Hydroamination. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b02559
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AUTHORS (5)
SA
Syed T. Ahmed
FP
Fabio Parmeggiani
NW
Nicholas J. Weise
SF
Sabine
L. Flitsch
NT
Nicholas J. Turner
KEYWORDS
deracemization cascadel-heteroarylalaninebiocatalystPureanaloguePALconversionl-pyridylalaninestrategyeemethodologyRing-Substitutednitrogen-containing heteroarylalaninesenantiopurityaldehydecomplementphenylalanine ammonia lyaseprotectionAnabaena variabilisBiocatalytic Hydroaminationmultistep synthesisyieldpurificationSynthesiEnantiomerically