Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids.

Akula Akula,Kwon Kwon

doi:10.3390/biom9100566

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.

Highlights

The development of green chemicals, bioplastics, bioactive compounds, pharmaceuticals, and cosmetics from sustainable biomass is an emerging trend in chemistry and related industries.For example, thermoplastic elastomers (TPEs) that show similar properties as those of plastics and rubbery materials can be used as biodegradable plastics [1]
Omega-dicarboxylic acids have been used as precursors or building blocks for the synthesis of interesting bioactive compounds such as inhibitors of
We previously reported on bioenzymatic and chemical transformations of ricinoleic acid and oleic acid via their corresponding ester intermediates driven in E. coli cells

Summary

Introduction

The development of green chemicals, bioplastics, bioactive compounds, pharmaceuticals, and cosmetics from sustainable biomass is an emerging trend in chemistry and related industries.For example, thermoplastic elastomers (TPEs) that show similar properties as those of plastics and rubbery materials can be used as biodegradable plastics [1]. Omega-dicarboxylic acids and ω-aminocarboxylic acids of medium length (C7 to C13) have been widely used as intermediates or building blocks for the synthesis of hydraulic fluids, lubricants, pharmaceuticals, plasticizers, and TPEs [3,4,5,6,7]. Omega-dicarboxylic acids have been used as precursors or building blocks for the synthesis of interesting bioactive compounds such as inhibitors of CDK4/6-mediated cancer [8], DNA sequence-specific ligands [9], and hydroxyproline analogs showing anti-breast cancer activity [10]. Omega-aminocarboxylic acids including 11-aminoundecanoic acid are useful intermediates for the syntheses of fusidic acid derivatives [11], rolipram-type derivatives [12], and ocotillol-type derivatives [13] with interesting biological activities

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Conclusion