Biosynthesis and Biocatalysis

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

Deadline for manuscript submissions: closed (30 June 2021) | Viewed by 10586

Special Issue Editors


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Guest Editor
Department of Biochemistry, Molecular Biology and Biotechnology, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Interests: biotransformations; lipase-catalyzed reactions; hydroxyphosphonates; determination of the absolute configuration by NMR spectroscopy

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Guest Editor
Department of Biochemistry, Molecular Biology and Biotechnology, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Interests: xenobiotics biodegradation; fungal biocatalysts; nanoparticle biosynthesis

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Guest Editor
Department of Biochemistry, Molecular Biology and Biotechnology, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Interests: biotransformation; fungi; enantioselective transformation; optically pure phosphonates; biocatalytic synthesis

Special Issue Information

Dear Colleagues,

Biocatalysis has been established as the green alternative to traditional chemical synthesis because of the mild, controlled reaction conditions, shorter reaction time, lower energy consumption. and lower waste generation. The natural features of biocatalysts, such as chemo-, regio- and enantioselectivity, are an advantage over chemical procedures and are effectively used in industry. Despite the above, though, there are also many challenges to applying biological systems, which must be resolved. Biocatalysts are of moderate effectiveness toward xenobiotic substrates, which are converted into valuable starting materials for synthetic purposes. For this reason, it is important both to search for new ways of bioconversion and to use waste materials for the synthesis of commodity or fine chemicals and attractive chemical building blocks. The challenge of biocatalytic approaches to synthesis is to invent protocols allowing obtained products with good enantioselectivity (in the case of chiral substrates/products) and conversion degree. These can be achieved by a variety of approaches, such as proper biocatalyst screening, alteration of its activity by influencing of its form (e.g., immobilization) or by engineering of the culturing or/and reaction medium.

The aims of this Special Issue are as follows: biosynthesis of new compounds of defined interest, bioconversions carried with enzymes or/and whole-cell systems assistance, stereoselective biocatalysis, strategies of enantioselectivity control, scaling-up of bioprocesses, and the application of biocatalysis for biorefinery purposes.

Dr. Paulina Majewska
Dr. Magdalena Klimek-Ochab
Dr. Małgorzata Brzezińska-Rodak
Guest Editors

Manuscript Submission Information

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Keywords

  • Biosynthesis
  • Biocatalysis
  • Bioconversion
  • Biotransformation
  • Asymmetric synthesis
  • Kinetic resolution of racemic mixtures
  • Enantioselectivity
  • Biorefinery

Published Papers (5 papers)

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Research

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11 pages, 1937 KiB  
Article
Monapinone Coupling Enzyme Produces Non-Natural Heterodimers
by Satoshi Ohte, Masayuki Toyoda, Keisuke Kobayashi, Isao Fujii, Taichi Ohshiro and Hiroshi Tomoda
Catalysts 2021, 11(8), 1015; https://doi.org/10.3390/catal11081015 - 23 Aug 2021
Viewed by 1790
Abstract
The monapinone coupling enzyme (MCE), a fungal multicopper oxidase, catalyzes the regioselective C–C coupling between tricyclic monapinone A (the primary substrate) and other monapinones (secondary substrates) to produce atropisomeric biaryl homo- or heterodimers. In this study, mono-, bi- and tricyclic compounds were tested [...] Read more.
The monapinone coupling enzyme (MCE), a fungal multicopper oxidase, catalyzes the regioselective C–C coupling between tricyclic monapinone A (the primary substrate) and other monapinones (secondary substrates) to produce atropisomeric biaryl homo- or heterodimers. In this study, mono-, bi- and tricyclic compounds were tested to determine whether they worked as secondary substrates for MCE. Among 14 cyclic compounds, MCE utilized semivioxanthin, YWA1, 1,3-naphthalenediol and flaviolin as secondary substrates to produce non-natural heterodimers. The atropisomeric biaryl heterodimers produced by MCE from monapinone A and semivioxanthin were isolated, and their structures were elucidated by NMR and MS. These findings indicate that MCE recognizes bi- and tricyclic compounds with a 1,3-dihydroxy or 1-hydroxy-3-methoxy benzene ring as a secondary substrate. Full article
(This article belongs to the Special Issue Biosynthesis and Biocatalysis)
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10 pages, 1474 KiB  
Article
Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates
by Paulina Majewska
Catalysts 2021, 11(8), 956; https://doi.org/10.3390/catal11080956 - 10 Aug 2021
Viewed by 1565
Abstract
The main objective of this study is the enantioselective synthesis of carboxyhydroxyphosphonates by lipase-catalyzed reactions. For this purpose, racemic dimethyl and dibutyl 1-butyryloxy-1-carboxymethylphosphonates were synthesized and hydrolyzed, using a wide spectrum of commercially available lipases from different sources (e.g., fungi and bacteria). The [...] Read more.
The main objective of this study is the enantioselective synthesis of carboxyhydroxyphosphonates by lipase-catalyzed reactions. For this purpose, racemic dimethyl and dibutyl 1-butyryloxy-1-carboxymethylphosphonates were synthesized and hydrolyzed, using a wide spectrum of commercially available lipases from different sources (e.g., fungi and bacteria). The best hydrolysis results of dimethyl 1-butyryloxy-1-carboxymethylphosphonate were obtained with the use of lipases from Candida rugosa, Candida antarctica, and Aspergillus niger, leading to optically active dimethyl 1-carboxy-1-hydroxymethylphosphonate (58%–98% enantiomeric excess) with high enantiomeric ratio (reaching up to 126). However, in the case of hydrolysis of dibutyl 1-butyryloxy-1-carboxymethylphosphonate, the best results were obtained by lipases from Burkholderia cepacia and Termomyces lanuginosus, leading to optically active dibutyl 1-carboxy-1-hydroxymethylphosphonate (66%–68% enantiomeric excess) with moderate enantiomeric ratio (reaching up to 8.6). The absolute configuration of the products after biotransformation was also determined. In most cases, lipases hydrolyzed (R) enantiomers of both compounds. Full article
(This article belongs to the Special Issue Biosynthesis and Biocatalysis)
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14 pages, 22113 KiB  
Article
Quality of Emulsions Containing Fat Blends Modified by Enzymatic Catalysis
by Małgorzata Kowalska, Magdalena Woźniak, Anna Zbikowska, Eva Ivanišová and Artur Molik
Catalysts 2021, 11(4), 453; https://doi.org/10.3390/catal11040453 - 31 Mar 2021
Cited by 1 | Viewed by 1436
Abstract
The purpose of this study was to evaluate the effect of the enzymatic modification of muton tallow and hemp seed oil fat blends. An attempt of application of these fat blends as fat phases in emulsion systems with various amount of carboxymethylcellulose was [...] Read more.
The purpose of this study was to evaluate the effect of the enzymatic modification of muton tallow and hemp seed oil fat blends. An attempt of application of these fat blends as fat phases in emulsion systems with various amount of carboxymethylcellulose was made. Fat blends before and after enzymatic catalysis were assessed in the context of polar and non-polar fractions content, antioxidant activity, oxidative stability and texture. Emulsions were investigated in the terms of their stability, color, microstructure, droplets diameter, and viscosity. The study revealed that emulsions containing as a fat phases modified blends with greater share of mutton tallow showed more favorable properties, and greater stability. The presented emulsions are a model dispersion system, after adjustment of the additives they could be used as chemical, food or cosmetic products. Full article
(This article belongs to the Special Issue Biosynthesis and Biocatalysis)
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Review

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16 pages, 2296 KiB  
Review
Cyanobacteria as Valuable Tool in Biotechnology
by Agnieszka Śliżewska and Ewa Żymańczyk-Duda
Catalysts 2021, 11(11), 1259; https://doi.org/10.3390/catal11111259 - 20 Oct 2021
Cited by 5 | Viewed by 2283
Abstract
Cyanobacteria constitute an interesting group of photosynthetic microorganisms due to their morphological and genetic diversity that is related to their extremely long evolution process, which created the need for them to adapt to immensely heterogeneous environmental conditions. Cyanobacteria grow in salt and fresh [...] Read more.
Cyanobacteria constitute an interesting group of photosynthetic microorganisms due to their morphological and genetic diversity that is related to their extremely long evolution process, which created the need for them to adapt to immensely heterogeneous environmental conditions. Cyanobacteria grow in salt and fresh waters as well as on the surface of soils and rocks. The diverse cell structure is characterized by the fact that they occur in many morphological forms, from small single cells through to larger ones as well as branches, threads, or spirals. Taking into account the presence of cyanobacteria in virtually all possible conditions and places on Earth, cyanobacteria represent an unexplored potential that is worth investigating. This review presents the possibilities of using algae in chosen areas of biotechnology: e.g., as biocatalysts or in industries such as the pharmaceutical industry. It covers the characteristics of secondary metabolites along with their division and the potential of using them as sources of effective drugs for many diseases. It presents an overview of the possibilities of using cyanobacteria in biotransformation processes. These processes are of great importance in the case of, for example, the neutralization of municipal, industrial, or chemical waste, the amount of which is constantly growing every year, and they are also an easier and cheaper path to obtain chemical compounds. Full article
(This article belongs to the Special Issue Biosynthesis and Biocatalysis)
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26 pages, 3011 KiB  
Review
Altering the Stereoselectivity of Whole-Cell Biotransformations via the Physicochemical Parameters Impacting the Processes
by Agnieszka Raczyńska, Joanna Jadczyk and Małgorzata Brzezińska-Rodak
Catalysts 2021, 11(7), 781; https://doi.org/10.3390/catal11070781 - 27 Jun 2021
Cited by 3 | Viewed by 2613
Abstract
The enantioselective synthesis of organic compounds is one of the great challenges in organic synthetic chemistry due to its importance for the acquisition of biologically active derivatives, e.g., pharmaceuticals, agrochemicals, and others. This is why biological systems are increasingly applied as tools for [...] Read more.
The enantioselective synthesis of organic compounds is one of the great challenges in organic synthetic chemistry due to its importance for the acquisition of biologically active derivatives, e.g., pharmaceuticals, agrochemicals, and others. This is why biological systems are increasingly applied as tools for chiral compounds synthesis or modification. The use of whole cells of “wild-type” microorganisms is one possible approach, especially as some methods allow improving the conversion degrees and controlling the stereoselectivity of the reaction without the need to introduce changes at the genetic level. Simple manipulation of the culture conditions, the form of a biocatalyst, or the appropriate composition of the biotransformation medium makes it possible to obtain optically pure products in a cheap, safe, and environmentally friendly manner. This review contains selected examples of the influence of physicochemical factors on the stereochemistry of the biocatalytic preparation of enantiomerically pure compounds, which is undertaken through kinetically controlled separation of their racemic mixtures or reduction of prochiral ketones and has an effect on the final enantiomeric purity and enantioselectivity of the reaction. Full article
(This article belongs to the Special Issue Biosynthesis and Biocatalysis)
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