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Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade
Amination of non-activated aliphatic fatty alcohols to the corresponding primary amines was achieved through a five-enzyme cascade reaction by coupling a long-chain alcohol oxidase from Aspergillus fumigatus (LCAO_Af) with a ω-transaminase from Chromobacterium violaceum (ω-TA_Cv). The alcohol was ox...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Blackwell Publishing Ltd
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4641459/ https://www.ncbi.nlm.nih.gov/pubmed/26583050 http://dx.doi.org/10.1002/cctc.201500589 |
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author | Pickl, Mathias Fuchs, Michael Glueck, Silvia M Faber, Kurt |
author_facet | Pickl, Mathias Fuchs, Michael Glueck, Silvia M Faber, Kurt |
author_sort | Pickl, Mathias |
collection | PubMed |
description | Amination of non-activated aliphatic fatty alcohols to the corresponding primary amines was achieved through a five-enzyme cascade reaction by coupling a long-chain alcohol oxidase from Aspergillus fumigatus (LCAO_Af) with a ω-transaminase from Chromobacterium violaceum (ω-TA_Cv). The alcohol was oxidized at the expense of molecular oxygen to yield the corresponding aldehyde, which was subsequently aminated by the PLP-dependent ω-TA to yield the final primary amine product. The overall cascade was optimized with respect to pH, O(2) pressure, substrate concentration, decomposition of H(2)O(2) (derived from alcohol oxidation), NADH regeneration, and biocatalyst ratio. The substrate scope of this concept was investigated under optimized conditions by using terminally functionalized C(4)–C(11) fatty primary alcohols bearing halogen, alkyne, amino, hydroxy, thiol, and nitrile groups. |
format | Online Article Text |
id | pubmed-4641459 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Blackwell Publishing Ltd |
record_format | MEDLINE/PubMed |
spelling | pubmed-46414592015-11-16 Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade Pickl, Mathias Fuchs, Michael Glueck, Silvia M Faber, Kurt ChemCatChem Communications Amination of non-activated aliphatic fatty alcohols to the corresponding primary amines was achieved through a five-enzyme cascade reaction by coupling a long-chain alcohol oxidase from Aspergillus fumigatus (LCAO_Af) with a ω-transaminase from Chromobacterium violaceum (ω-TA_Cv). The alcohol was oxidized at the expense of molecular oxygen to yield the corresponding aldehyde, which was subsequently aminated by the PLP-dependent ω-TA to yield the final primary amine product. The overall cascade was optimized with respect to pH, O(2) pressure, substrate concentration, decomposition of H(2)O(2) (derived from alcohol oxidation), NADH regeneration, and biocatalyst ratio. The substrate scope of this concept was investigated under optimized conditions by using terminally functionalized C(4)–C(11) fatty primary alcohols bearing halogen, alkyne, amino, hydroxy, thiol, and nitrile groups. Blackwell Publishing Ltd 2015-10 2015-09-03 /pmc/articles/PMC4641459/ /pubmed/26583050 http://dx.doi.org/10.1002/cctc.201500589 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by/4.0/ This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Pickl, Mathias Fuchs, Michael Glueck, Silvia M Faber, Kurt Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade |
title | Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade |
title_full | Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade |
title_fullStr | Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade |
title_full_unstemmed | Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade |
title_short | Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade |
title_sort | amination of ω-functionalized aliphatic primary alcohols by a biocatalytic oxidation–transamination cascade |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4641459/ https://www.ncbi.nlm.nih.gov/pubmed/26583050 http://dx.doi.org/10.1002/cctc.201500589 |
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