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Biocatalytic Synthesis of Bioactive Compounds • Josefina Aleu Biocatalytic Synthesis of Bioactive Compounds Biocatalytic Bioactive of Compounds Synthesis • Josefina Aleu Biocatalytic Synthesis of Bioactive Compounds Edited by Josefina Aleu Printed Edition of the Special Issue Published in Molecules www.mdpi.com/journal/molecules Biocatalytic Synthesis of Bioactive Compounds Biocatalytic Synthesis of Bioactive Compounds Editor Josefina Aleu MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade • Manchester • Tokyo • Cluj • Tianjin Editor Josefina Aleu University of Cadiz´ Spain Editorial Office MDPI St. Alban-Anlage 66 4052 Basel, Switzerland This is a reprint of articles from the Special Issue published online in the open access journal Molecules (ISSN 1420-3049) (available at: https://www.mdpi.com/journal/molecules/special issues/Biocatalytic Synthesis). For citation purposes, cite each article independently as indicated on the article page online and as indicated below: LastName, A.A.; LastName, B.B.; LastName, C.C. Article Title. Journal Name Year, Article Number, Page Range. ISBN 978-3-03943-571-5 (Hbk) ISBN 978-3-03943-572-2 (PDF) c 2020 by the authors. Articles in this book are Open Access and distributed under the Creative Commons Attribution (CC BY) license, which allows users to download, copy and build upon published articles, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. The book as a whole is distributed by MDPI under the terms and conditions of the Creative Commons license CC BY-NC-ND. Contents About the Editor .............................................. vii Preface to ”Biocatalytic Synthesis of Bioactive Compounds” .................... ix Te-Sheng Chang, Tzi-Yuan Wang, Szu-Yi Yang, Yu-Han Kao, Jiumn-Yih Wu and Chien-Min Chiang Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of Deinococcus geothermalis Reprinted from: Molecules 2019, 24, 2236, doi:10.3390/molecules24122236 .............. 1 Alexander Veljko Fejzagi´c, Jan Gebauer, Nikolai Huwa and Thomas Classen Halogenating Enzymes for Active Agent Synthesis: First Steps Are Done and Many Have to Follow Reprinted from: Molecules 2019, 24, 4008, doi:10.3390/molecules24214008 .............. 13 Jainara Santos do Nascimento, Wilson Elias Rozo N u´ nez,˜ Valmore Henrique Pereira dos Santos, Josefina Aleu, S´ılvio Cunha and Eliane de Oliveira Silva Mapping the Biotransformation of Coumarins through Filamentous Fungi Reprinted from: Molecules 2019, 24, 3531, doi:10.3390/molecules24193531 .............. 47 Jascha Rolf, Mattijs K. Julsing, Katrin Rosenthal and Stephan Lutz ¨ A Gram-Scale Limonene Production Process with Engineered Escherichia coli Reprinted from: Molecules 2020, 25, 1881, doi:10.3390/molecules25081881 .............. 57 Nina-Katharina Krahe, Ralf G. Berger and Franziska Ersoy A DyP-Type Peroxidase of Pleurotus sapidus with Alkene Cleaving Activity Reprinted from: Molecules 2020, 25, 1536, doi:10.3390/molecules25071536 .............. 69 Young Sung Jung, Ye-Jin Kim, Aaron Taehwan Kim, Davin Jang, Mi-Seon Kim, Dong-Ho Seo, Tae Gyu Nam, Chan-Su Rha, Cheon-Seok Park and Dae-Ok Kim Enrichment of Polyglucosylated Isoflavones from S oybean I soflavone Ag lycones Using Optimized Amylosucrase Transglycosylation Reprinted from: Molecules 2020, 25, 181, doi:10.3390/molecules25010181 .............. 87 Elisabetta Brenna, Danilo Colombo, Giuseppe Di Lecce, Francesco G. Gatti, Maria Chiara Ghezzi, Francesca Tentori, Davide Tessaro and Mariacristina Viola Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route Reprinted from: Molecules 2020, 25, 1882, doi:10.3390/molecules25081882 ..............103 Mateusz Kutyła, Jan Fiedurek, Anna Gromada, Krzysztof Jedrzejewski and Mariusz Trytek Mutagenesis and Adaptation of the Psychrotrophic Fungus Chrysosporium pannorum A-1 as a Method for Improving β-pinene Bioconversion Reprinted from: Molecules 2020, 25, 2589, doi:10.3390/molecules25112589 ..............115 v About the Editor Josefina Aleu studied Chemistry at the University of Cadiz,´ where she graduated in 1991. After working with Prof. J. R. Hanson at Sussex University for several months in 1995, she then completed her Ph.D. degree in 1996 under the supervision of Prof. Collado on the design of selective fungicides. She then worked for 15 months as a postdoctoral fellow with Prof. C. Fuganti at Politecnico di Milano (Italy) on the biocatalytic synthesis of flavors. She is currently Senior Lecturer of Organic Chemistry at the University of Cadiz,´ and her current research interests are directed towards the biocatalytic synthesis of bioactive molecules, design of selective fungicides, and studies of the metabolism of marine microorganisms. vii Preface to ”Biocatalytic Synthesis of Bioactive Compounds” Biocatalysis, the application of enzymes as catalysts for chemical synthesis, has become an increasingly valuable tool for the synthetic chemist. Enzymatic transformations carried out by partially purified e nzymes or w hole-cell c atalysts are u sed for the p roduction of a w ide variety of compounds ranging from bulk to fine c hemicals. In the fi eld of fin e che micals, the main application clearly lies in the exploitation of the outstanding properties of these biocatalysts with respect to chemoselectivity, regioselectivity, and especially stereoselectivity in the production of enantiomerically pure compounds. Until recently, chemical development companies regarded biocatalysis as a method to be attempted only when all other chemical options failed. Currently, there are clear signs that this view is changing radically, with many of the new process developments revealing the benefits to be gained by using biocatalysis on a commercial scale. Biocatalytic processes have a number of advantages over the corresponding chemical methods. The conditions for such processes are mild and, in the majority of cases, do not require the protection of other functional groups. Moreover, eliminating the need for several chemical synthetic steps has had a dramatic impact on the overall economics. In many cases, biological methods are also enantiospecific, allowing for the production of chiral products from racemic mixtures. Furthermore, the features governing their regiospecificity d iffer from t hose c ontrolling c hemical s pecificity an d, in deed, it is possible to obtain biotransformations at centers that are chemically unreactive. Economically, biocatalytic processes are often cheaper and more direct than their chemical counterparts, and the conversions normally proceed under conditions that are regarded as ecologically acceptable. The aim of this Special Issue is to present studies focused on biocatalysis as applied to the organic synthesis of bioactive compounds and their precursors. The obtained contributions deal with biotransformations, including the stereoselective synthesis of bioactive chemical compounds, active pharmaceutical ingredients, and natural products. The production of interesting bioactive compounds is covered in the eight articles comprising seven research articles and a review. Two of these papers deal with fungal metabolism and fungi-mediated biotransformations. The first paper deals with improving β-pinene bioconversion by mutagenesis and adaptation of the fungus Chrysosporium pannorum A-1. A second paper describes a study on the biotransformation of bioactive coumarins by filamentous fungi. On the other hand, the conversion of oleic acid into azelaic and pelargonic acid by a chemoenzymatic route represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. In addition, the findings on a gram-scale limonene production process using engineered Escherichia coli provide a basis for the development of an economic and industrially relevant bioprocess. Alkene cleavage is a possibility to generate aldehydes with olfactory properties for the fragrance and flavor i ndustry. A dye-decolorizing peroxidase (DyP) of the basidiomycete Pleurotus sapidus is the first described DyP with alkene cleavage activity towards aryl alkenes and showed potential as biocatalyst for flavor production. Isoflavones in soybeans are well-known p hytoestrogens. Soy isoflavones present in conjugated forms are converted to aglycone forms during processing and storage. Isoflavone aglycones (IFAs) of soybeans in human diets have poor solubility in water, resulting in low bioavailability and bioactivity. Enzyme-mediated glycosylation is an efficient and e nvironmentally f riendly way to ix modify the physicochemical properties of soy IFAs. Thus, Jung et al. studied the enrichment of polyglucosylated isoflavones from soybean isoflavone aglycones using optimized amylosucrase transglycosylation. In the same line, Chang et al. studied the potential industrial production of a well-soluble, alkaline-stable, and anti-inflammatory isoflavone glucoside from 8-hydroxydaidzein glucosylated by recombinant amylosucrase of Deinococcus geothermalis. Finally, the review discusses the use of halogenating enzymes in fine chemical syntheses, detailing the many steps that are still needed before halogenating enzymes are considered reliable, flexible, and sustainable catalysts for halogenation. Overall, these eight contributions provide the reader with relevant fresh insights into the use of enzymes and whole cells as biocatalysts. Josefina Aleu Editor x molecules Article Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory
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