Cargando…
Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases
The amination of alcohols is an important transformation in chemistry. The redox‐neutral (i.e., hydrogen‐borrowing) asymmetric amination of alcohols is enabled by the combination of an alcohol dehydrogenase (ADH) with an amine dehydrogenase (AmDH). In this work, we enhanced the efficiency of hydroge...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5837013/ https://www.ncbi.nlm.nih.gov/pubmed/29515675 http://dx.doi.org/10.1002/cctc.201701366 |
_version_ | 1783304049853988864 |
---|---|
author | Böhmer, Wesley Knaus, Tanja Mutti, Francesco G. |
author_facet | Böhmer, Wesley Knaus, Tanja Mutti, Francesco G. |
author_sort | Böhmer, Wesley |
collection | PubMed |
description | The amination of alcohols is an important transformation in chemistry. The redox‐neutral (i.e., hydrogen‐borrowing) asymmetric amination of alcohols is enabled by the combination of an alcohol dehydrogenase (ADH) with an amine dehydrogenase (AmDH). In this work, we enhanced the efficiency of hydrogen‐borrowing biocatalytic amination by co‐immobilizing both dehydrogenases on controlled porosity glass Fe(III) ion‐affinity beads. The recyclability of the dual‐enzyme system was demonstrated (5 cycles) with total turnover numbers of >4000 and >1000 for ADH and AmDH, respectively. A set of (S)‐configured alcohol substrates was aminated with up to 95 % conversion and >99 % ee (R). Preparative‐scale amination of (S)‐phenylpropan‐2‐ol resulted in 90 % conversion and 80 % yield of the product in 24 h. |
format | Online Article Text |
id | pubmed-5837013 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-58370132018-03-05 Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases Böhmer, Wesley Knaus, Tanja Mutti, Francesco G. ChemCatChem Communications The amination of alcohols is an important transformation in chemistry. The redox‐neutral (i.e., hydrogen‐borrowing) asymmetric amination of alcohols is enabled by the combination of an alcohol dehydrogenase (ADH) with an amine dehydrogenase (AmDH). In this work, we enhanced the efficiency of hydrogen‐borrowing biocatalytic amination by co‐immobilizing both dehydrogenases on controlled porosity glass Fe(III) ion‐affinity beads. The recyclability of the dual‐enzyme system was demonstrated (5 cycles) with total turnover numbers of >4000 and >1000 for ADH and AmDH, respectively. A set of (S)‐configured alcohol substrates was aminated with up to 95 % conversion and >99 % ee (R). Preparative‐scale amination of (S)‐phenylpropan‐2‐ol resulted in 90 % conversion and 80 % yield of the product in 24 h. John Wiley and Sons Inc. 2018-01-11 2018-02-21 /pmc/articles/PMC5837013/ /pubmed/29515675 http://dx.doi.org/10.1002/cctc.201701366 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Böhmer, Wesley Knaus, Tanja Mutti, Francesco G. Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases |
title | Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases |
title_full | Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases |
title_fullStr | Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases |
title_full_unstemmed | Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases |
title_short | Hydrogen‐Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases |
title_sort | hydrogen‐borrowing alcohol bioamination with coimmobilized dehydrogenases |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5837013/ https://www.ncbi.nlm.nih.gov/pubmed/29515675 http://dx.doi.org/10.1002/cctc.201701366 |
work_keys_str_mv | AT bohmerwesley hydrogenborrowingalcoholbioaminationwithcoimmobilizeddehydrogenases AT knaustanja hydrogenborrowingalcoholbioaminationwithcoimmobilizeddehydrogenases AT muttifrancescog hydrogenborrowingalcoholbioaminationwithcoimmobilizeddehydrogenases |