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Asymmetric and Selective Biocatalysis catalysts Asymmetric and Selective Biocatalysis Edited by Jose M. Palomo and Cesar Mateo Printed Edition of the Special Issue Published in Catalysts www.mdpi.com/journal/catalysts Asymmetric and Selective Biocatalysis Asymmetric and Selective Biocatalysis Special Issue Editors Jose M. Palomo Cesar Mateo MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade Special Issue Editors Jose M. Palomo Cesar Mateo Group of Chemical Biology and Biocatalysis Group of Chemical Processes Catalyzed by enzymes Departament of Biocatalysis Departament of Biocatalysis Institute of Catalysis (ICP-CSIC) Institute of Catalysis (ICP-CSIC) Spain 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 Catalysts (ISSN 2073-4344) from 2016 to 2017 (available at: https://www.mdpi.com/journal/catalysts/special issues/selective biocatalysis) 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 978-3-03897-846-6 (Pbk) ISBN 978-3-03897-847-3 (PDF) c 2019 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 Special Issue Editors ..................................... vii Preface to ”Asymmetric and Selective Biocatalysis” ......................... ix Cesar Mateo and Jose M. Palomo Asymmetric and Selective Biocatalysis Reprinted from: Catalysts 2018, 8, 588, doi:10.3390/catal8120588 ................... 1 Paola Vitale, Antonia Digeo, Filippo Maria Perna, Gennaro Agrimi, Antonio Salomone, Antonio Scilimati, Cosimo Cardellicchio and Vito Capriati Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted † Oxygen-Containing Heterocycles Reprinted from: Catalysts 2017, 7, 37, doi:10.3390/catal7020037 .................... 4 Robson Carlos Alnoch, Ricardo Rodrigues de Melo, Jose M. Palomo, Emanuel Maltempi de Souza, Nadia Krieger and Cesar Mateo New Tailor-Made Alkyl-Aldehyde Bifunctional Supports for Lipase Immobilization Reprinted from: Catalysts 2016, 6, 191, doi:10.3390/catal6120191 ................... 17 Cintia W. Rivero and Jose M. Palomo Covalent Immobilization of Candida rugosa Lipase at Alkaline pH and Their Application in the Regioselective Deprotection of Per-O-acetylated Thymidine Reprinted from: Catalysts 2016, 6, 115, doi:10.3390/catal6080115 ................... 30 Yajie Wang and Huimin Zhao Tandem Reactions Combining Biocatalysts and Chemical Catalysts for Asymmetric Synthesis Reprinted from: Catalysts 2016, 6, 194, doi:10.3390/catal6120194 ................... 41 Anika Scholtissek, Dirk Tischler, Adrie H. Westphal, Willem J. H. van Berkel and Caroline E. Paul Old Yellow Enzyme-Catalysed Asymmetric Hydrogenation: Linking Family Roots with Improved Catalysis Reprinted from: Catalysts 2017, 7, 130, doi:10.3390/catal7050130 ................... 62 Su-Yan Wang, Pedro Laborda, Ai-Min Lu, Xu-Chu Duan, Hong-Yu Ma, Li Liu and Josef Voglmeir N-acetylglucosamine 2-Epimerase from Pedobacter heparinus: First Experimental Evidence of a Deprotonation/Reprotonation Mechanism Reprinted from: Catalysts 2016, 6, 212, doi:10.3390/catal6120212 ................... 86 Christian Herrero, Nhung Nguyen-Thi, Fabien Hammerer, Fr´ed´ericBanse, Donald Gagn´e, Nicolas Doucet, Jean-Pierre Mahy and R´emyRicoux Photoassisted Oxidation of Sulfides Catalyzed by Artificial Metalloenzymes Using Water as † an Oxygen Source Reprinted from: Catalysts 2016, 6, 202, doi:10.3390/catal6120202 ...................102 Forest H. Andrews, Cindy Wechsler, Megan P. Rogers, Danilo Meyer, Kai Tittmann and Michael J. McLeish Mechanistic and Structural Insight to an Evolved Benzoylformate Decarboxylase with Enhanced Pyruvate Decarboxylase Activity Reprinted from: Catalysts 2016, 6, 190, doi:10.3390/catal6120190 ...................114 v Xin Wang, Li Yang, Weijia Cao, Hanxiao Ying, Kequan Chen and Pingkai Ouyang Efficient Production of Enantiopure D-Lysine from L-Lysine by a Two-Enzyme Cascade System Reprinted from: Catalysts 2016, 6, 168, doi:10.3390/catal6110168 ...................131 vi About the Special Issue Editors Jose M. Palomo was born in Coin, Malaga, Spain (1976). He received his bachelor’s degree in Chemistry in 1999 from the Universidad Autonoma de Madrid (UAM) as a Spanish government fellow. After graduation, he joined Guisan’s group at Institute of Catalysis (ICP, CSIC) in Madrid to complete his doctoral studies. He received his Ph.D. degree (summa cum laude) in 2003. His Ph.D. thesis developed novel highly efficient immobilized biocatalysts for asymmetric transformations and strategies for understanding the biochemical features of lipases. As an EMBO postdoctoral fellow, Jose pursued training in solid-phase peptide synthesis and semisynthetic protein preparation with Herbert Waldmann at the Chemical Biology Department of the Max Planck Institute in Dortmund from 2004 to 2006. In 2006, he began his appointment as Associate Research Scientist at Biocatalysis Department in ICP-CSIC. From 2009, he has been an Associate Professor (Tenured Scientist) in ICP-CSIC. Jose has published more than 140 articles in high-impact journals, with more than 7000 times cited and an H index of 42. Cesar Mateo was born in 1969 and he did his PhD in the Catalysis Institute (ICP-CSIC), receiving the title in 2001 in the Autonoma University (Madrid, Spain). After a period of study in Marseille with Prof. Furstoss and in Delft with Prof. Sheldon, he started working in ICP. He is an Associate Professor (Tenured Scientist) in the ICP. He has focused his career in developing different immobilization technologies to obtain heterogeneous biocatalysts with improved properties. The catalysts have been used for different biotransformations, developing sensors (based on enzymes, antibodies, or DNA probes), or in other fields such as in biomedical applications and others. As principal contributions, he is the author of 164 articles in SCI journals, more than 20 book chapters, and 14 patents, with an H index of 53. The papers have been cited more than 9800 times in different journals. vii Preface to ”Asymmetric and Selective Biocatalysis” The synthesis of compounds or chiral building blocks with the desired configuration is one of the greatest challenges of chemistry, and is of the great interest in fields such as analytical chemistry and especially in fine and pharmaceutical chemistry. For this, different biocatalysts (i.e., cells, enzymes, catalytic antibodies, or ribozymes) have been used to catalyze different processes used, even on an industrial scale. Biocatalysts have a high activity under very mild conditions, such as ambient temperature, neutral pH, and atmospheric pressure. They are also able to catalyze highly selective and specific modifications in different substrates with high complexity, allowing the synthesis of enantiomerically pure compounds either by resolution processes or by asymmetric synthesis from prochiral substrates or regioselective modifications in complex molecules. This avoids side reactions as well as costly purification processes. In addition to the pure biocatalysts that are traditionally used, in recent years, different hybrid catalysts have been developed that combine the good catalytic properties of traditional biocatalysts with the properties of organometallic catalysts. In this way, different mixed catalysts have been developed as artificial metalloenzymes combining enzymatic and metallic catalytic activities, expanding the applicability to different systems, such as cascade processes. Jose M. Palomo, Cesar Mateo Special Issue Editors ix catalysts Editorial Asymmetric and Selective Biocatalysis Cesar Mateo * and Jose M. Palomo * Department of Biocatalysis, Institute of Catalysis (ICP-CSIC), Marie Curie 2, Cantoblanco, Campus UAM, 28049 Madrid, Spain * Correspondence: [email protected] (C.M.); [email protected] (J.M.P.); Tel.: +34-915-854-768 (C.M. & J.M.P.) Received: 14 November 2018; Accepted: 15 November 2018; Published: 28 November 2018 The synthesis of compounds or chiral building-blocks with the desired configuration is one of the greatest challenges of chemistry and is of great interest in different fields such as analytical chemistry and especially in fine and pharmaceutical chemistry. Different biocatalysts (cells, enzymes, catalytic antibodies, or ribozymes) have been used to catalyze different processes, even on an industrial scale. Biocatalysts have high activity under very mild conditions such as ambient temperature, neutral pH, and atmospheric pressure. They are also able to catalyze highly selective and specific modifications in different substrates with high complexity, allowing the synthesis of enantiomerically pure compounds either by resolution processes or by asymmetric synthesis from prochiral substrates or regioselective modifications in complex molecules. This avoids side reactions as well as costly purification processes. In recent years, in addition to the pure biocatalysts traditionally used, different hybrid catalysts have been developed, which combine the
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