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Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids
In addition to our previous efforts toward bioenzymatic and chemical transformations of ricinoleic acid and oleic acid to their corresponding α,ω-dicarboxylic acids via their ester intermediates driven in Escherichia coli cells, several efficient oxidation conditions were investigated and optimized...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6843907/ https://www.ncbi.nlm.nih.gov/pubmed/31590242 http://dx.doi.org/10.3390/biom9100566 |
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author | Akula, Ravi Kumar Kwon, Yong-Uk |
author_facet | Akula, Ravi Kumar Kwon, Yong-Uk |
author_sort | Akula, Ravi Kumar |
collection | PubMed |
description | In addition to our previous efforts toward bioenzymatic and chemical transformations of ricinoleic acid and oleic acid to their corresponding α,ω-dicarboxylic acids via their ester intermediates driven in Escherichia coli cells, several efficient oxidation conditions were investigated and optimized for the conversion of ω-hydroxycarboxylic acids to α,ω-dicarboxylic acids. Pd/C-catalyzed oxidation using NaBH(4) in a basic aqueous alcohol and Ni(II) salt-catalyzed oxidation using aqueous sodium hypochlorite were considered to be excellent as a hybrid reaction for three successive chemical reactions (hydrogenation, hydrolysis, and oxidation) and an eco-friendly, cost-effective, and practical approach, respectively. Omega-hydroxycarboxylic acids and ω-aminocarboxylic acid were also easily prepared as useful building blocks for plastics or bioactive compounds from the bioenzymatically driven ester intermediate. The scope of the developed synthetic methods can be utilized for large-scale synthesis and various derivatizations. |
format | Online Article Text |
id | pubmed-6843907 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-68439072019-11-25 Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids Akula, Ravi Kumar Kwon, Yong-Uk Biomolecules Article In addition to our previous efforts toward bioenzymatic and chemical transformations of ricinoleic acid and oleic acid to their corresponding α,ω-dicarboxylic acids via their ester intermediates driven in Escherichia coli cells, several efficient oxidation conditions were investigated and optimized for the conversion of ω-hydroxycarboxylic acids to α,ω-dicarboxylic acids. Pd/C-catalyzed oxidation using NaBH(4) in a basic aqueous alcohol and Ni(II) salt-catalyzed oxidation using aqueous sodium hypochlorite were considered to be excellent as a hybrid reaction for three successive chemical reactions (hydrogenation, hydrolysis, and oxidation) and an eco-friendly, cost-effective, and practical approach, respectively. Omega-hydroxycarboxylic acids and ω-aminocarboxylic acid were also easily prepared as useful building blocks for plastics or bioactive compounds from the bioenzymatically driven ester intermediate. The scope of the developed synthetic methods can be utilized for large-scale synthesis and various derivatizations. MDPI 2019-10-04 /pmc/articles/PMC6843907/ /pubmed/31590242 http://dx.doi.org/10.3390/biom9100566 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Akula, Ravi Kumar Kwon, Yong-Uk Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids |
title | Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids |
title_full | Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids |
title_fullStr | Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids |
title_full_unstemmed | Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids |
title_short | Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids |
title_sort | bioenzymatic and chemical derivatization of renewable fatty acids |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6843907/ https://www.ncbi.nlm.nih.gov/pubmed/31590242 http://dx.doi.org/10.3390/biom9100566 |
work_keys_str_mv | AT akularavikumar bioenzymaticandchemicalderivatizationofrenewablefattyacids AT kwonyonguk bioenzymaticandchemicalderivatizationofrenewablefattyacids |