Synthesis of Enantiomerically Pure Ring-Substituted l-Pyridylalanines by Biocatalytic HydroaminationCitation formats

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@article{6f84b5eb837946edb4f9b121513066e0,
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.",
author = "Syed Ahmed and Fabio Parmeggiani and Nicholas Weise and Sabine Flitsch and Nicholas Turner",
year = "2016",
doi = "10.1021/acs.orglett.6b02559",
language = "English",
journal = "Organic Letters",
issn = "1523-7052",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Synthesis of Enantiomerically Pure Ring-Substituted l-Pyridylalanines by Biocatalytic Hydroamination

AU - Ahmed, Syed

AU - Parmeggiani, Fabio

AU - Weise, Nicholas

AU - Flitsch, Sabine

AU - Turner, Nicholas

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.6b02559

DO - 10.1021/acs.orglett.6b02559

M3 - Article

JO - Organic Letters

JF - Organic Letters

SN - 1523-7052

ER -