<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles

The active pharmaceutical ingredient levetiracetam has anticonvulsant properties and is used to treat epilepsies. Herein, we describe the enantioselective preparation of the levetiracetam precursor 2-(pyrrolidine-1-yl)butanamide by enzymatic dynamic kinetic resolution with a nitrile hydratase enzyme...

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Autores principales:	Birgit Grill, Melissa Horvat, Helmut Schwab, Ralf Gross, Kai Donsbach, Margit Winkler
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	small molecule dynamic kinetic resolution levetiracetam nitrile hydratase amino amide amino nitrile Chemical technology TP1-1185 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/806021d901a34b0cb1bbf25b458befe4
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id	oai:doaj.org-article:806021d901a34b0cb1bbf25b458befe4
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spelling	oai:doaj.org-article:806021d901a34b0cb1bbf25b458befe42021-11-25T17:05:28Z<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles10.3390/catal111112872073-4344https://doaj.org/article/806021d901a34b0cb1bbf25b458befe42021-10-01T00:00:00Zhttps://www.mdpi.com/2073-4344/11/11/1287https://doaj.org/toc/2073-4344The active pharmaceutical ingredient levetiracetam has anticonvulsant properties and is used to treat epilepsies. Herein, we describe the enantioselective preparation of the levetiracetam precursor 2-(pyrrolidine-1-yl)butanamide by enzymatic dynamic kinetic resolution with a nitrile hydratase enzyme. A rare representative of the family of iron-dependent nitrile hydratases from <i>Gordonia hydrophobica</i> (<i>Gh</i>NHase) was evaluated for its potential to form 2-(pyrrolidine-1-yl)butanamide in enantioenriched form from the three small, simple molecules, namely, propanal, pyrrolidine and cyanide. The yield and the enantiomeric excess (<i>ee</i>) of the product are determined most significantly by the substrate concentrations, the reaction pH and the biocatalyst amount. <i>Gh</i>NHase is also active for the hydration of other nitriles, in particular for the formation of <i>N</i>-heterocyclic amides such as nicotinamide, and may therefore be a tool for the preparation of various APIs.Birgit GrillMelissa HorvatHelmut SchwabRalf GrossKai DonsbachMargit WinklerMDPI AGarticlesmall moleculedynamic kinetic resolutionlevetiracetamnitrile hydrataseamino amideamino nitrileChemical technologyTP1-1185ChemistryQD1-999ENCatalysts, Vol 11, Iss 1287, p 1287 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	small molecule dynamic kinetic resolution levetiracetam nitrile hydratase amino amide amino nitrile Chemical technology TP1-1185 Chemistry QD1-999
spellingShingle	small molecule dynamic kinetic resolution levetiracetam nitrile hydratase amino amide amino nitrile Chemical technology TP1-1185 Chemistry QD1-999 Birgit Grill Melissa Horvat Helmut Schwab Ralf Gross Kai Donsbach Margit Winkler <i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles
description	The active pharmaceutical ingredient levetiracetam has anticonvulsant properties and is used to treat epilepsies. Herein, we describe the enantioselective preparation of the levetiracetam precursor 2-(pyrrolidine-1-yl)butanamide by enzymatic dynamic kinetic resolution with a nitrile hydratase enzyme. A rare representative of the family of iron-dependent nitrile hydratases from <i>Gordonia hydrophobica</i> (<i>Gh</i>NHase) was evaluated for its potential to form 2-(pyrrolidine-1-yl)butanamide in enantioenriched form from the three small, simple molecules, namely, propanal, pyrrolidine and cyanide. The yield and the enantiomeric excess (<i>ee</i>) of the product are determined most significantly by the substrate concentrations, the reaction pH and the biocatalyst amount. <i>Gh</i>NHase is also active for the hydration of other nitriles, in particular for the formation of <i>N</i>-heterocyclic amides such as nicotinamide, and may therefore be a tool for the preparation of various APIs.
format	article
author	Birgit Grill Melissa Horvat Helmut Schwab Ralf Gross Kai Donsbach Margit Winkler
author_facet	Birgit Grill Melissa Horvat Helmut Schwab Ralf Gross Kai Donsbach Margit Winkler
author_sort	Birgit Grill
title	<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles
title_short	<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles
title_full	<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles
title_fullStr	<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles
title_full_unstemmed	<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles
title_sort	<i>gordonia hydrophobica</i> nitrile hydratase for amide preparation from nitriles
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/806021d901a34b0cb1bbf25b458befe4
work_keys_str_mv	AT birgitgrill igordoniahydrophobicainitrilehydrataseforamidepreparationfromnitriles AT melissahorvat igordoniahydrophobicainitrilehydrataseforamidepreparationfromnitriles AT helmutschwab igordoniahydrophobicainitrilehydrataseforamidepreparationfromnitriles AT ralfgross igordoniahydrophobicainitrilehydrataseforamidepreparationfromnitriles AT kaidonsbach igordoniahydrophobicainitrilehydrataseforamidepreparationfromnitriles AT margitwinkler igordoniahydrophobicainitrilehydrataseforamidepreparationfromnitriles
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<i>Gordonia hydrophobica</i> Nitrile Hydratase for Amide Preparation from Nitriles

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