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Synthesis of Two-Photon Sensitive Pro-Fluorescent Photoremovable Protecting Groups Elie Abou Nakad

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Synthesis of Two-Photon Sensitive Pro-Fluorescent Photoremovable Protecting Groups Elie Abou Nakad Synthesis of two-photon sensitive pro-fluorescent photoremovable protecting groups Elie Abou Nakad To cite this version: Elie Abou Nakad. Synthesis of two-photon sensitive pro-fluorescent photoremovable protecting groups. Organic chemistry. Université de Strasbourg, 2018. English. NNT : 2018STRAF039. tel-02160511 HAL Id: tel-02160511 https://tel.archives-ouvertes.fr/tel-02160511 Submitted on 19 Jun 2019 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. UNIVERSITÉ DE STRASBOURG ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES Laboratoire de Conception et Application de Molécules Bioactives (CAMB) UMR7199 THÈSE présentée par : Elie ABOU NAKAD Soutenue le : 16 Novembre 2018 pour obtenir le grade de : DoCteur de l’Université de Strasbourg Discipline/ Spécialité : Chimie Organique Synthèse de groupements proteCteurs photolabiles pro-fluoresCents sensibles à l’excitation bi-photonique THÈSE dirigée Par : M SPECHT Alexandre Directeur de recherche au CNRS, Université de Strasbourg RAPPORTEURS : Mme JOSEPH DelPhine Professeur, Université de Paris-Sud Mme MAHUTEAU-BETZER Florence Directeur de recherche au CNRS, Institut Curie-Orsay AUTRES MEMBRES DU JURY : M BLANC Aurélien Chargé de recherche au CNRS, Université de Strasbourg UNIVERSITÉ DE STRASBOURG ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES Laboratoire de Conception et Application de Molécules Bioactives (CAMB) UMR7199 THÈSE présentée par : Elie ABOU NAKAD Soutenue le : 16 Novembre 2018 pour obtenir le grade de : DoCteur de l’Université de Strasbourg Discipline/ Spécialité : Chimie Organique Synthèse de groupements proteCteurs photolabiles pro-fluoresCents sensibles à l’excitation bi-photonique THÈSE dirigée Par : M SPECHT Alexandre Directeur de recherche au CNRS, Université de Strasbourg RAPPORTEURS : Mme JOSEPH DelPhine Professeur, Université de Paris-Sud Mme MAHUTEAU-BETZER Florence Directeur de recherche au CNRS, Institut Curie-Orsay AUTRES MEMBRES DU JURY : M BLANC Aurélien Chargé de recherche au CNRS, Université de Strasbourg “Teach me knowledge and good judgment, for I trust your commands.” Psalms 119:66 To my lovely late Aunt Salwa, You’ve always believed in me This is my gift to you... ACKNOWLEDGEMENTS All the thesis work presented in this manuscript was done in the lab of “Conception et Applications des Molécules Bioactives” in the Chimie et Neurobiologie Moléculaire” group at the Faculty of Pharmacy of Strasbourg under the direction of Dr Alexandre SPECHT. First of all, I would like to express my sincere gratitude to the jury members: Prof Delphine JOSEPH, Dr Florence MAHUTEAU-BETZER and Dr Aurélien BLANC, for accepting to evaluate this thesis work and also for spending important time in reading this manuscript. Alexandre, or as you like us to call you, Alex, I have a lot to thank you for. I want to thank you for accepting me to be a PhD student in your lab and putting your trust in me that I can do the best for this project. A big thank you for all the help you gave me since the day of my arrival, with all the paper work and the administrative stuff. I am so grateful to have had a director like you; thank you for all the time you spend with me on “chemical discussions” as well as “polymer chain mass calculations” … Thanks to you, my knowledge on chemistry has grown day after day and my skills have evolved a lot. I am so glad that we were able to get the most out of this project. You will always be the “big brother who’s watching me”. Endless thanks for you! Fred, I would like to thank you for all the time you put in doing the photophysical analysis and thank you for the 20 fluorophores you gave me to decorate my bench. Thank you for all the help in understanding the wide world of photophysics and for giving me a lot of your expertise in the domain. It was always a pleasure working with you with all your English-French-Italian sense of humor and even though you are a busy man thank you for making everything “EASY!”. Thomas, thanks a lot for your wisdom and for sharing with us your highly-respected knowledge. Thank you for always being there when I had hesitations in biology and thank you for all the advice and because of you I know a lot on the historical part of Strasbourg. Thierry, Le Jeune, thank you for making every single lab meeting a stress-less time, thank you for always giving us the push to continue and thank you for all the rich discussions we had. Juline, my labmate, you were always saying time is going by slowly, now we’ve reached the end of this 3-year journey, we started together, and we are graduating together…Thank you for being the funniest labmate, thank you for reminding me when it is time to eat. Thank you for being beside me in all the hard times and thanks for helping me organize all the lab activities (including the unforgettable Pancakes Party). I wish you, from the bottom of my heart, all the best in your endeavors. I would like to thank as well, Bastien and Laurie for making the lab a great working atmosphere and thank you for all the help and fruitful discussion we had. You stood beside me since my arrival to the lab, you will always be the best labmates and the dearest friends. I wish you all the best in your future jobs. Kate, I wish you also all the best in your PhD, you still have time to change your mind…I guess… I will miss you correcting my American English with your British one. Thank you for making me memorize all your iTunes library. Wish you all the success and perseverance. I would like to thank all the lab members who worked with me during these 3 years: Florian, Lucas, Clément and Benoit. A sincere thank you for Philippe and Elodie who worked with me as master students, the project gave amazing results during your presence and with your help. Best of luck in your PhDs. Issam and Lodi (Les Issas) thank you for being my family in France and thank you for all the help and care and for making me discover lots of places in Alsace. You made this period the best time of my life, with you I have never felt far away from home. And to my 3 little siblings: Timothé, Pauline and Elena, I love you! I would like to thank as well: Dr Halim, Dr Ghina, Dr Eliane, and the future Drs Fatima, Elias, Naimah, and my friends: Carole, Alexa, Dima, Fadi, Mireille and the long list of friends who stayed beside me and supported me especially during the writing period. You guys are the best! To my everlasting support my aunt Hayat and the 2 best cousins: Tony and Rawad, thank you for always believing that I can do the best and for supporting me throughout the 8 years of chemistry. You are the greatest gift in my life! To my biggest support rock, my brother, Georges, thank you for being there for me all these times, and thank you for making me laugh when I was in need. To my childhood friend, Miray, you are the sister that I never had, you are the one of the most amazing souls I know, thank you for standing by my side at all times. To my nephew, Charbel, thank you for bringing joy to my life and thank you for making me the luckiest uncle in the world. You are my second family, I love you all. To my parents, Roukos and Hiam, you have waited a lot for this moment, I am sure that as much as I say, it will not be enough. Thank you for the full support, thank you for staying beside me all this time, thank you for believing in me and having faith in my skills. It is because of you that I had this chance and because of your endless prayers I reached this moment. Thank you for standing by my side in the hard times and the good times. It is to you that I owe my success. You’ve sacrificed a lot in order to make my dream a reality and today my dream, and your dream, is coming true. I respectfully love you! My first, last and forever thanks are to you, my biggest teacher. You gave me a lot since day 1 and now, I am giving you this work to bless it as you blessed my entire life… None of this would have been possible without you…I am grateful for you endlessly…GOD! Table of Contents CHAPTER I ................................................................................................................................................... 1 1. Photoremovable Protecting Groups (PPGs) ......................................................................................... 2 1.1. Definition: ............................................................................................................................................. 2 1.2. Requirements: ........................................................................................................................................ 2 1.3. Types of PPGs ....................................................................................................................................... 3 1.3.1. Benzoin PPGs ............................................................................................................................... 3 1.3.2. Arylcarbonylmethyl or Phenacyls (Pac) ....................................................................................... 4 1.3.3. Coumarin-4-ylmethyl ...................................................................................................................
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