Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution

Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were s...

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Detalles Bibliográficos
Autores principales: Sakulsombat, Morakot, Vongvilai, Pornrapee, Ramström, Olof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4497319/
https://www.ncbi.nlm.nih.gov/pubmed/25055970
http://dx.doi.org/10.1002/chem.201402615
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author Sakulsombat, Morakot
Vongvilai, Pornrapee
Ramström, Olof
author_facet Sakulsombat, Morakot
Vongvilai, Pornrapee
Ramström, Olof
author_sort Sakulsombat, Morakot
collection PubMed
description Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates.
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spelling pubmed-44973192015-07-10 Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution Sakulsombat, Morakot Vongvilai, Pornrapee Ramström, Olof Chemistry Communications Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates. WILEY-VCH Verlag 2014-09-01 2014-07-23 /pmc/articles/PMC4497319/ /pubmed/25055970 http://dx.doi.org/10.1002/chem.201402615 Text en 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the terms of Creative Commons Attribution NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Communications
Sakulsombat, Morakot
Vongvilai, Pornrapee
Ramström, Olof
Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution
title Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution
title_full Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution
title_fullStr Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution
title_full_unstemmed Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution
title_short Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α-Aminonitrile Resolution
title_sort efficient asymmetric synthesis of 1-cyano-tetrahydroisoquinolines from lipase dual activity and opposite enantioselectivities in α-aminonitrile resolution
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4497319/
https://www.ncbi.nlm.nih.gov/pubmed/25055970
http://dx.doi.org/10.1002/chem.201402615
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