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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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1365-3075
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Application of bio-based solvents for biocatalysed synthesis of amides with Pseudomonas stutzeri lipase (PSL)

Giulia Paggiola
  • Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, North Yorkshire YO10 5DD, UK
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/ Nolwenn Derrien / Jonathan D. Moseley / Anthony Green
  • Manchester Institute of Biotechnology & School of Chemistry, The University of Manchester, Manchester, M1 7DN, UK
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/ Sabine L. Flitsch
  • Manchester Institute of Biotechnology & School of Chemistry, The University of Manchester, Manchester, M1 7DN, UK
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/ James H. Clark
  • Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, North Yorkshire YO10 5DD, UK
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/ Con Robert McElroy
  • Corresponding author
  • Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, North Yorkshire YO10 5DD, UK
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/ Andrew J. HuntORCID iD: https://orcid.org/0000-0003-3983-8313
Published Online: 2019-12-19 | DOI: https://doi.org/10.1515/pac-2019-0808

Abstract

Bio-based solvents were investigated for the biocatalysed amidation reactions of various ester-amine combinations by Pseudomonas stutzeri lipase (PSL). Reactions were undertaken in a range of green and potentially bio-based solvents including terpinolene, p-cymene, limonene, 2-methyl THF, ɣ-valerolactone, propylene carbonate, dimethyl isosorbide, glycerol triacetate and water. Solvent screenings demonstrated the importance and potential of using non-polar bio-based solvents for favouring aminolysis over hydrolysis; whilst substrate screenings highlighted the unfavourable impact of reactants bearing bulky para- or 4-substituents. Renewable terpene-based solvents (terpinolene, p-cymene, D-limonene) were demonstrated to be suitable bio-based media for PSL amidation reactions. Such solvents could provide a greener and more sustainable alternative to traditional petrochemical derived non-polar solvents. Importantly, once the enzyme (either PSL or CALB) binds with a bulky para-substituted substrate, only small reagents are able to access the active site. This therefore limits the possibility for aminolysis to take place, thereby promoting the hydrolysis. This mechanism of binding supports the widely accepted ‘Ping Pong – Bi Bi’ mechanism used to describe enzyme kinetics. The work highlights the need to further investigate enzyme activity in relation to para- or 4-substituted substrates. A priority in PSL chemistry remains a methodology to tackle the competing hydrolysis reaction.

This article offers supplementary material which is provided at the end of the article.

Keywords: amides; bio-based; biocatalysis; biocatalysts; enzyme catalysis; fine chemicals; green chemistry; ICGC-8; organic chemistry; organic synthesis; pharmaceuticals; solvents; sustainable chemistry

Article note

A collection of invited papers based on presentations at the 8th IUPAC International Conference on Green Chemistry (ICGC-8), Bangkok, Thailand, 9–14 September 2018.

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About the article

Published Online: 2019-12-19


Funding Source: Thailand Research Fund

Award identifier / Grant number: RSA6280031

Andrew Hunt would like to acknowledge the financial support of the Thailand Research Fund (Funder Id: http://dx.doi.org/10.13039/501100004396, RSA6280031) and Khon Kaen University. Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation is gratefully acknowledged. The research leading to these results has received funding from the Innovative Medicines Initiative (http://www.imi.europa.eu) Joint Undertaking under Funder Id: http://dx.doi.org/10.13039/501100010767, grant agreement no. 115360, resources of which are composed of the financial contribution from the European Union’s Seventh Framework Programme (FP7/2007-2013) and EFPIA companies in kind contribution.


Citation Information: Pure and Applied Chemistry, 20190808, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2019-0808.

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©2019 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/.Get Permission

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