Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin
Every year, a large amount of residual agroindustrial waste has been generated and only around 10% is in fact reused. The development of new strategies for biomass valorization is important to add value to these commodities, since biomass is an excellent alternative feedstock to obtain chemicals of...
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ftdoajarticles:oai:doaj.org/article:9b876b06ad484673bf5170d6d93fe5b5 2023-05-15T13:55:38+02:00 Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin Marcelo Avelar do Nascimento Larissa Ester Gotardo Eduardo Miguez Bastos Fabio C. L. Almeida Raquel A. C. Leão Rodrigo O. M. A. de Souza Robert Wojcieszak Ivaldo Itabaiana 2019-10-01T00:00:00Z https://doi.org/10.3390/su11216044 https://doaj.org/article/9b876b06ad484673bf5170d6d93fe5b5 EN eng MDPI AG https://www.mdpi.com/2071-1050/11/21/6044 https://doaj.org/toc/2071-1050 2071-1050 doi:10.3390/su11216044 https://doaj.org/article/9b876b06ad484673bf5170d6d93fe5b5 Sustainability, Vol 11, Iss 21, p 6044 (2019) levoglucosan calb lipase immobilization noediff transesterification esters Environmental effects of industries and plants TD194-195 Renewable energy sources TJ807-830 Environmental sciences GE1-350 article 2019 ftdoajarticles https://doi.org/10.3390/su11216044 2022-12-31T15:23:57Z Every year, a large amount of residual agroindustrial waste has been generated and only around 10% is in fact reused. The development of new strategies for biomass valorization is important to add value to these commodities, since biomass is an excellent alternative feedstock to obtain chemicals of interest from renewable resources. The major compound of pyrolytic treatment of lignocellulosic biomass is levoglucosan (1,6-anhydroglucopyranose), an anhydro-sugar that can be transformed into glucose and is greatly valued in the most diverse industrial sectors as a surfactant, emulsifier, or even a lubricant. In this work, levoglucosan was acylated by lipase-catalyzed transesterification in acetonitrile with great conversions and selectivities with different acyl donors such as ethyl esters of lauric, palmitic, stearic, and oleic acids prepared in situ in an integrated strategy mediated by commercial lipases Novozym435 (N435), PSIM, and the home-made biocatalyst CaLB_epoxy. As a result, all biocatalyst generated mostly monoesters, with N435 being more selective to produce lauric esters (99% at 50°C) and PSIM to produce oleic esters (97% at 55 °C) while CaLB_epoxy was more selective to produce oleic esters of levoglucosan (83% at 55°C). This is the first report in the literature on the production of high selectivity levoglucosan esters. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Sustainability 11 21 6044 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
levoglucosan calb lipase immobilization noediff transesterification esters Environmental effects of industries and plants TD194-195 Renewable energy sources TJ807-830 Environmental sciences GE1-350 |
spellingShingle |
levoglucosan calb lipase immobilization noediff transesterification esters Environmental effects of industries and plants TD194-195 Renewable energy sources TJ807-830 Environmental sciences GE1-350 Marcelo Avelar do Nascimento Larissa Ester Gotardo Eduardo Miguez Bastos Fabio C. L. Almeida Raquel A. C. Leão Rodrigo O. M. A. de Souza Robert Wojcieszak Ivaldo Itabaiana Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
topic_facet |
levoglucosan calb lipase immobilization noediff transesterification esters Environmental effects of industries and plants TD194-195 Renewable energy sources TJ807-830 Environmental sciences GE1-350 |
description |
Every year, a large amount of residual agroindustrial waste has been generated and only around 10% is in fact reused. The development of new strategies for biomass valorization is important to add value to these commodities, since biomass is an excellent alternative feedstock to obtain chemicals of interest from renewable resources. The major compound of pyrolytic treatment of lignocellulosic biomass is levoglucosan (1,6-anhydroglucopyranose), an anhydro-sugar that can be transformed into glucose and is greatly valued in the most diverse industrial sectors as a surfactant, emulsifier, or even a lubricant. In this work, levoglucosan was acylated by lipase-catalyzed transesterification in acetonitrile with great conversions and selectivities with different acyl donors such as ethyl esters of lauric, palmitic, stearic, and oleic acids prepared in situ in an integrated strategy mediated by commercial lipases Novozym435 (N435), PSIM, and the home-made biocatalyst CaLB_epoxy. As a result, all biocatalyst generated mostly monoesters, with N435 being more selective to produce lauric esters (99% at 50°C) and PSIM to produce oleic esters (97% at 55 °C) while CaLB_epoxy was more selective to produce oleic esters of levoglucosan (83% at 55°C). This is the first report in the literature on the production of high selectivity levoglucosan esters. |
format |
Article in Journal/Newspaper |
author |
Marcelo Avelar do Nascimento Larissa Ester Gotardo Eduardo Miguez Bastos Fabio C. L. Almeida Raquel A. C. Leão Rodrigo O. M. A. de Souza Robert Wojcieszak Ivaldo Itabaiana |
author_facet |
Marcelo Avelar do Nascimento Larissa Ester Gotardo Eduardo Miguez Bastos Fabio C. L. Almeida Raquel A. C. Leão Rodrigo O. M. A. de Souza Robert Wojcieszak Ivaldo Itabaiana |
author_sort |
Marcelo Avelar do Nascimento |
title |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_short |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_full |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_fullStr |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_full_unstemmed |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_sort |
regioselective acylation of levoglucosan catalyzed by candida antarctica (calb) lipase immobilized on epoxy resin |
publisher |
MDPI AG |
publishDate |
2019 |
url |
https://doi.org/10.3390/su11216044 https://doaj.org/article/9b876b06ad484673bf5170d6d93fe5b5 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Sustainability, Vol 11, Iss 21, p 6044 (2019) |
op_relation |
https://www.mdpi.com/2071-1050/11/21/6044 https://doaj.org/toc/2071-1050 2071-1050 doi:10.3390/su11216044 https://doaj.org/article/9b876b06ad484673bf5170d6d93fe5b5 |
op_doi |
https://doi.org/10.3390/su11216044 |
container_title |
Sustainability |
container_volume |
11 |
container_issue |
21 |
container_start_page |
6044 |
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1766262413932363776 |