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Effectors of Selectivity in Laccase Catalyzed Reactions Lu Ren Effectors of selectivity in laccase catalyzed reactions Lu Ren To cite this version: Lu Ren. Effectors of selectivity in laccase catalyzed reactions. Catalysis. Ecole Centrale Marseille, 2019. English. NNT : 2019ECDM0013. tel-03080959 HAL Id: tel-03080959 https://tel.archives-ouvertes.fr/tel-03080959 Submitted on 18 Dec 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. École Doctorale – Sciences Chimiques ED250 Institut des sciences moléculaires de Marseille (iSm2)-BiosCiences THÈSE DE DOCTORAT pour obtenir le grade de DOCTEUR de l’ÉCOLE CENTRALE de MARSEILLE Discipline : Chimie TITRE DE LA THÈSE : Effectors of selectivity in laccase catalyzed reactions Par REN Lu Directeur de thèse : Thierry TRON Co-Directeur de thèse: Dr. Pierre ROUSSELOT-PAILLEY Soutenue le 17 décembre 2019 devant le jury composé de : Maître de conferences Mme. Belèn ALBELA Rapporteur (École normale supérieure de Lyon) Directrice de recherche Mme. Christine CAVAZZA Rapporteur (CEA Grenoble) Directeur de Recherche CNRS Mme. Ling PENG Examinateur (Aix-Marseille Université) Directeur de Recherche CNRS M. Thierry TRON Directeur de thèse (Aix-Marseille Université) Chargé de recherche CNRS Mme. Karine HEUZE Invitée (Université de Bordeaux) Chargé de recherche CNRS Co-directeur de M. Pierre ROUSSELOT-PAILLEY (Aix-Marseille Université) thèse, Invitée To my motherland, Much distress regenerates a nation, May we defeat the 2019 novel coronavirus soon. École Doctorale – Sciences Chimiques ED250 Institut des sciences moléculaires de Marseille (iSm2)-BiosCiences THÈSE DE DOCTORAT pour obtenir le grade de DOCTEUR de l’ÉCOLE CENTRALE de MARSEILLE Discipline : Chimie TITRE DE LA THÈSE : Effectors of selectivity in laccase catalyzed reactions Par REN Lu Directeur de thèse : Thierry TRON Co-Directeur de thèse: Dr. Pierre ROUSSELOT-PAILLEY Soutenue le 17 décembre 2019 devant le jury composé de : Maître de conferences Mme. Belèn ALBELA Rapporteur (École normale supérieure de Lyon) Directrice de recherche Mme. Christine CAVAZZA Rapporteur (CEA Grenoble Center) Directeur de Recherche CNRS Mme. Ling PENG Examinateur (Aix-Marseille Université) Directeur de Recherche CNRS M. Thierry TRON Directeur de thèse (Aix-Marseille Université) Chargé de recherche CNRS Mme. Karine HEUZE Invitée (Université de Bordeaux) Chargé de recherche CNRS Co-directeur de M. Pierre ROUSSELOT-PAILLEY (Aix-Marseille Université) thèse, Invitée ACKNOWLEDGEMENTS The completion of the challenge for a doctoral degree, apart from my personal endeavor, would not be possible without the continuous help and encouragement from the people mentally or spatially around me. I would like to express my gratitude to them. First, I would like to give my great thanks to professor Marius REGLIER. About four years ago, he seriously forwarded my email about PhD position inquiry to professor Thierry TRON, which indirectly gave me the opportunity to work in Institute des Sciences Moléculaires de Marseille (ISM2). And it is the beginning of all the story. I also owe my deepest gratitude to my supervisor, professor Thierry TRON. I thank him for his professional advice and guidance during my research. Throughout these three years, he encouraged me countless times when I did not obtain the desired experiment results and doubted myself. I am especially grateful for him in believing in me, motivating me to be a real scientist. My sincere gratitude extends to my co-supervisor Dr. Pierre Rousselot-PAILLEY, for his important help during the whole process of my PhD. He actively helped me solving the problems I encountered in the project and trained me with great patience in the experimental operation, I really appreciated his tolerance and kindness to me. I would like to express my sincere thanks to Dr. Yasmina MEKMOUCHE and Dr. Simeng ZHOU, for their active participation in the discussions of my topic and providing valuable advice to my research. They shared me with their energy, which made me never give up. Many thanks and greetings to my colleagues in the lab ISM2 BiosCiences. I particularly thank Dr. MARESCA Marc for his advice on ELISA; thank Dr. FAURE Bruno for his technical support of the FTIR machine and other equipment, thank Dr. Viviane ROBERT, Ms. Agnes AMOURIC, Ms. Elise COURVOISIER-DEZORD and Ms. Yolande CHARMASSON for helping me in the culture of Pichia pastoris during AtDIR6 production, thank Dr. Michael LAFOND and Dr. Christophe DECROOS for their guidance and discussions on the purification of AtDIR6, as well as the use of FPLC, Maybe I can’t list here all the people and the good things they have done for me, but I will always remember their selfless and patient help. My thanks also go to my officemates for the friendship and enjoyment they provided to me. Especially Ms. Alessia MUNZONE, she was always willing to help me either in the specialist area or in life with pressure, I regard her as one of my best friends. I acknowledge the hospitality of Dr. Karine HEUZE during my stay in Bordeaux. I thank her and her PhD student Mr. HongTao JI for their help in providing magnetic particles for my experiment and helping us to do a series of characterizations of the particles. Sincere appreciation is also acknowledged to my thesis committee: Professor Christine CAVAZZA, Professor Belèn ALBELA, Professor Ling PENG, for their insightful comments and kind encouragement. The deepest gratitude to my most loyal friends around me in France, including Mr. Jie ZHANG, Ms. Dan FENG, Ms. Fangfang YANG, Ms. Xiaoxi PAN, Ms. Wenjing YANG, Ms. Lan YANG, Ms. Qi WANG, Mr. Rui LIU, Mr. Lingyu KONG, Mr. Guochao GAO, Mr. Jian YANG and forth. They have offered me invaluable help both in my academic and casual life, we shared the joys and sorrows in Marseille. I am thankful to their companion and encouragement, tolerance and patience along the way. The days we struggle together will be remembered forever. My PhD study would not be possible without the unconditional support of my loved families, I really thank them for understanding my will to pursue my dream, and for forgiving me for being absent in each of the full moon days for three years, while these special days, I should be there with them. Last but not least, the financial support provided by the Chinese Scholarship Council (China) is gratefully acknowledged. Résumé Résumé Aujourd'hui la nécessité d'un développement durable de la société humaine et les problèmes écologiques, environnementaux et économiques associés ont suscité une inquiétude généralisée au sein de la communauté internationale. Par conséquent, une grande attention est accordée à la chimie verte, aux technologies propres et aux processus respectueux de l'environnement. L'économie respectueuse de l'environnement devient le principal moteur de l'innovation technologique, qui pose de nouveaux défis à la chimie, en particulier la chimie de synthèse. Des réglementations plus strictes ont été introduites pour protéger l'environnement par les gouvernements du monde entier, incitant l'industrie chimique à se concentrer sur l'élimination ou la réduction de la production de déchets à la source. Cela entraînera inévitablement de nouvelles exigences pour la science et la technologie des produits chimiques et leurs processus de production. L'un des moyens les plus importants d'atteindre ces objectifs est la catalyse, sous ces diverses formes allant de la catalyse chimique à la biocatalyse. Un processus catalytique est un processus qui augmente la vitesse d'une réaction chimique en ajoutant une substance appelée catalyseur, qui peut effectuer une réaction de façon répétée sans être consommée dans le processus.1 Par conséquent, la catalyse est considérée comme un processus à forte économie d’atomes et est donc considérée comme verte. La catalyse joue un rôle important dans la société moderne. Un bon exemple est l'évolution du processus de production de la lazabemide (un médicament contre la maladie de Parkinson) développé par F. Hoffmann-La Roche AG. Le processus de synthèse initial comprenait 8 étapes avec un rendement de 8%, le schéma de synthèse a été ramené à une étape en faisant appel à un catalyseur au palladium avec un rendement global de 65%.2 Jusqu'à présent, un grand nombre de types de catalyseurs sont utilisés dans le commerce, notamment des catalyseurs hétérogènes (solides poreux), des catalyseurs homogènes (dissous dans le mélange réactionnel liquide), des catalyseurs biologiques (sous forme d'enzymes).3 Respectueux de l'environnement, des exemples de catalyse combinant à la fois une catalyse hétérogène ou homogène et enzymatique sont apparus récemment. Les processus catalytiques verts impliquent que les processus chimiques soient rendus respectueux de l'environnement en tirant parti des rendements élevés et de la sélectivité possibles pour les produits cibles, avec peu ou pas de produits secondaires indésirables et aussi souvent une efficacité énergétique élevée.4 Vu la demande croissante de catalyse respectueuse de l'environnement, la biocatalyse est un élément incontournable. Le catalyseur (une enzyme) lui-même est fabriqué à partir
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