Bioenzymatic and chemical derivatization of renewable fatty acids

Ravi Kumar Akula, Yong Uk Kwon

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

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 NaBH4 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.

Original languageEnglish
Article number566
JournalBiomolecules
Volume9
Issue number10
DOIs
StatePublished - Oct 2019

Bibliographical note

Funding Information:
Funding: This study was supported by the Marine Biomaterials Research Center grant from the Marine Biotechnology Program funded by the Ministry of Oceans and Fisheries, Republic of Korea (No. D11013214H480000100). R.K.A. was partially supported by the BK21 PLUS Program from the National Research Foundation of Korea (NRF).

Funding Information:
This study was supported by the Marine Biomaterials Research Center grant from the Marine Biotechnology Program funded by the Ministry of Oceans and Fisheries, Republic of Korea (No. D11013214H480000100). R.K.A. was partially supported by the BK21 PLUS Program from the National Research Foundation of Korea (NRF).

Publisher Copyright:
© 2019 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

  • Biocatalysis
  • Biomass
  • Fatty acid
  • Oxidation
  • α
  • ω-amino acid
  • ω-dicarboxylic acid

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