Biocatalysis in Lipids Modification

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Biocatalysis".

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 12502

Special Issue Editors


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Guest Editor
Department of Chemistry, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, Poland
Interests: enzymatic modifications and chemical synthesis of phospholipids; biocatalysis; bioactive fatty acids; conjugated linoleic acid – methods of synthesis and separation of isomers; drug delivery systems based on phospholipids and lipid nanoparticles

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Guest Editor
Department of Chemistry, Wrocław University of Environmental and Life Sciences, 50-375, Wrocław, Poland
Interests: enzymatic modifications of natural lipids and phospholipids; chemoenzymatic synthesis of structured lipids; biocatalysis; biologically active fatty acids; lipase and phospholipase-catalyzed resolution of racemic secondary alcohols

Special Issue Information

Dear Colleagues,

Lipids are a broad group of organic compounds that can be defined as small hydrophobic or amphiphilic molecules. The amphiphilic nature of some specific groups of lipids allows them to form vesicles, liposomes, or membranes in the aqueous environment. Natural lipids are synthesized in living organisms from two distinct types of subunits: ketoacyl or isoprene blocks. Therefore, lipids can be divided into eight groups: fatty acids, glycerolipids, glycerophospholipids, sphingolipids, glycolipids and polyketides, the derivatives of ketoacyl subunits condensation, and sterols and prenyl lipids that are formed by condensation of isoprenoid subunits. While the term "lipids" is sometimes used synonymously with fats, the latter are actually a subgroup of fats—triacylglycerols. This group of lipids is one of the most widely described in the scientific literature in terms of modification using biocatalysts. Lipases are the most established biocatalysts used for the modification of triacylglycerols and also phospholipids. Over the years, scientists have tried to understand the mechanism of action of lipases and used the acquired knowledge to develop efficient biocatalysts by immobilizing them or applying genetic engineering. Currently, enzymes with improved stability and selectivity are widely used in industry and science for the manufacturing of functional lipids with adjusted physicochemical or nutraceutical properties. These structured lipids have applications in food, pharmaceutical, cosmetics production.

This Special Issue is dedicated to new approaches in enzymatic biocatalysis or biotransformations of a wide range of lipids. It covers different types of reactions, such as esterification, hydrolysis, transesterification interesterification, oxidation, etc. catalyzed by native or genetically improved enzymes from different classes (lipases, phospholipases, oxygenases, hydratases, lipoxygenases, and lyases) or whole cells. Reviews and original research papers on the modification of acylglycerols, phospholipids, waxes, sterols, and prenyl lipids are welcome.

Dr. Natalia Niezgoda
Prof. Anna Chojnacka
Guest Editors

Manuscript Submission Information

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Keywords

  • biocatalysis
  • lipids modification
  • structured lipids
  • enzyme-catalyzed modification
  • new free or immobilized enzyme in lipids modification
  • lipases
  • phospholipases
  • lipid nanoparticles
  • biomolecules
  • biofuels

Published Papers (4 papers)

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Research

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13 pages, 1347 KiB  
Article
Integrated Cleaner Biocatalytic Process for Biodiesel Production from Crude Palm Oil Comparing to Refined Palm Oil
by Papasanee Muanruksa, Phavit Wongsirichot, James Winterburn and Pakawadee Kaewkannetra
Catalysts 2021, 11(6), 734; https://doi.org/10.3390/catal11060734 - 15 Jun 2021
Cited by 2 | Viewed by 2573
Abstract
An integrated cleaner biocatalyst process was performed for biodiesel production from crude palm oil (CPO) and refined palm oil (RPO). It was evaluated on process efficiency in terms of high purity of biodiesel as well as by-products without purification, less wastewater, less time [...] Read more.
An integrated cleaner biocatalyst process was performed for biodiesel production from crude palm oil (CPO) and refined palm oil (RPO). It was evaluated on process efficiency in terms of high purity of biodiesel as well as by-products without purification, less wastewater, less time consuming, and a simple downstream process. A first saponification step was carried out in both f CPO and RPO, a high purity of glycerol (86.25% and 87.5%) was achieved, respectively, while free fatty acids (FFASs) in soap were obtained after hexane extraction. High yields of FFASs were obtained from both CPO and RPO (98.83% and 90.94%). Subsequently, the FFAs were esterified to biodiesel by a biocatalyst of immobilized lipase. The highest biodiesel yields achieved were of 92.14% and 92.58% (CPO and RPO). Remarkably, biodiesel yields obtained from CPO and RPO achieved satisfactory values and the biocatalyst used could be reused for more than 16–17 cycles. Full article
(This article belongs to the Special Issue Biocatalysis in Lipids Modification)
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16 pages, 1983 KiB  
Article
Reactive Deep Eutectic Solvents (RDESs): A New Tool for Phospholipase D-Catalyzed Preparation of Phospholipids
by Chiara Allegretti, Francesco G. Gatti, Stefano Marzorati, Letizia Anna Maria Rossato, Stefano Serra, Alberto Strini and Paola D’Arrigo
Catalysts 2021, 11(6), 655; https://doi.org/10.3390/catal11060655 - 22 May 2021
Cited by 15 | Viewed by 3215
Abstract
The use of Reactive Deep Eutectic Solvents (RDESs) in the preparation of polar head modified phospholipids (PLs) with phospholipase D (PLD)-catalyzed biotransformations has been investigated. Natural phosphatidylcholine (PC) has been submitted to PLD-catalyzed transphosphatidylations using a new reaction medium composed by a mixture [...] Read more.
The use of Reactive Deep Eutectic Solvents (RDESs) in the preparation of polar head modified phospholipids (PLs) with phospholipase D (PLD)-catalyzed biotransformations has been investigated. Natural phosphatidylcholine (PC) has been submitted to PLD-catalyzed transphosphatidylations using a new reaction medium composed by a mixture of RDES/buffer. Instead of exploiting deep eutectic solvents conventionally, just as the reaction media, these solvents have been designed here in order to contribute actively to the synthetic processes by participating as reagents. RDESs were prepared using choline chloride or trimethyl glycine as hydrogen-bond acceptors and glycerol or ethylene glycol, as hydrogen-bond donors as well as nucleophiles for choline substitution. Specifically designed RDES/buffer reaction media allowed the obtainment of PLs with optimized yields in the perspective of a sustainable process implementation. Full article
(This article belongs to the Special Issue Biocatalysis in Lipids Modification)
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13 pages, 2159 KiB  
Article
Application of Immobilized Cholest-4-en-3-one Δ1-Dehydrogenase from Sterolibacterium Denitrificans for Dehydrogenation of Steroids
by Mateusz Tataruch, Patrycja Wójcik, Agnieszka M. Wojtkiewicz, Katarzyna Zaczyk, Katarzyna Szymańska and Maciej Szaleniec
Catalysts 2020, 10(12), 1460; https://doi.org/10.3390/catal10121460 - 14 Dec 2020
Cited by 3 | Viewed by 2279
Abstract
Cholest-4-en-3-one Δ1-dehydrogenase (AcmB) from Sterolibacterium denitrificans was successfully immobilized on 3-aminopropyltrimethoysilane functionalized mesoporous cellular foam (MCF) and Santa Barbara Amorphous (SBA-15) silica supports using adsorption or covalently with glutaraldehyde or divinyl sulfone linkers. The best catalyst, AcmB on MCF linked covalently [...] Read more.
Cholest-4-en-3-one Δ1-dehydrogenase (AcmB) from Sterolibacterium denitrificans was successfully immobilized on 3-aminopropyltrimethoysilane functionalized mesoporous cellular foam (MCF) and Santa Barbara Amorphous (SBA-15) silica supports using adsorption or covalently with glutaraldehyde or divinyl sulfone linkers. The best catalyst, AcmB on MCF linked covalently with glutaraldehyde, retained the specific activity of the homogenous enzyme while exhibiting a substantial increase of the operational stability. The immobilized enzyme was used continuously in the fed-batch reactor for 27 days, catalyzing 1,2-dehydrogenation of androst-4-en-3-one to androst-1,4-dien-3-one with a final yield of 29.9 mM (8.56 g/L) and 99% conversion. The possibility of reuse of the immobilized catalyst was also demonstrated and resulted in a doubling of the product amount compared to that in the reference homogenous reactor. Finally, it was shown that molecular oxygen from the air can efficiently be used as an electron acceptor either reoxidizing directly the enzyme or the reduced 2,4-dichlorophenolindophenol (DCPIPH2). Full article
(This article belongs to the Special Issue Biocatalysis in Lipids Modification)
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Review

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24 pages, 6002 KiB  
Review
Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review
by Adejanildo da S. Pereira, Aline Habibe de Souza, Jully L. Fraga, Pierre Villeneuve, Alexandre G. Torres and Priscilla F. F. Amaral
Catalysts 2022, 12(1), 88; https://doi.org/10.3390/catal12010088 - 13 Jan 2022
Cited by 22 | Viewed by 3429
Abstract
Lipases are versatile enzymes widely used in the pharmaceutical, cosmetic, and food industries. They are green biocatalysts with a high potential for industrial use compared to traditional chemical methods. In recent years, lipases have been used to synthesize a wide variety of molecules [...] Read more.
Lipases are versatile enzymes widely used in the pharmaceutical, cosmetic, and food industries. They are green biocatalysts with a high potential for industrial use compared to traditional chemical methods. In recent years, lipases have been used to synthesize a wide variety of molecules of industrial interest, and extraordinary results have been reported. In this sense, this review describes the important role of lipases in the synthesis of phytosterol esters, which have attracted the scientific community’s attention due to their beneficial effects on health. A systematic search for articles and patents published in the last 20 years with the terms “phytosterol AND esters AND lipase” was carried out using the Scopus, Web of Science, Scielo, and Google Scholar databases, and the results showed that Candida rugosa lipases are the most relevant biocatalysts for the production of phytosterol esters, being used in more than 50% of the studies. The optimal temperature and time for the enzymatic synthesis of phytosterol esters mainly ranged from 30 to 101 °C and from 1 to 72 h. The esterification yield was greater than 90% for most analyzed studies. Therefore, this manuscript presents the new technological approaches and the gaps that need to be filled by future studies so that the enzymatic synthesis of phytosterol esters is widely developed. Full article
(This article belongs to the Special Issue Biocatalysis in Lipids Modification)
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