Matthieu Sollogoub
2018; Wiley; Volume: 58; Issue: 7 Linguagem: Francês
10.1002/anie.201809650
ISSN1521-3773
Tópico(s)Fluorine in Organic Chemistry
ResumoAngewandte Chemie International EditionVolume 58, Issue 7 p. 1876-1877 Author ProfileFree Access Matthieu Sollogoub First published: 15 October 2018 https://doi.org/10.1002/anie.201809650AboutSectionsPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Graphical Abstract “My favorite molecule is glucose! The secret of being a successful scientist is being able to recognize luck when it strikes …” Find out more about Matthieu Sollogoub in his Author Profile. Matthieu Sollogoub The author presented on this page has recently published his 10th article in Angewandte Chemie in the last 10 years: “Bridging β-Cyclodextrin Prevents Self-Inclusion, Promotes Supramolecular Polymerization, and Promotes Cooperative Interaction with Nucleic Acids”: P. Evenou et al., Angew. Chem. Int. Ed. 2018, 57, 7753; Angew. Chem. 2018, 130, 7879. The work of M. Sollogoub has been featured as the frontispiece of Angewandte Chemie: “Can Hetero-Polysubstituted Cyclodextrins be Considered as Inherently Chiral Concave Molecules?”: S. Guieu, E. Zaborova, Y. Blériot, G. Poli, A. Jutand, D. Madec, G. Prestat, M. Sollogoub, Angew. Chem. Int. Ed. 2010, 49, 2314; Angew. Chem. 2010, 122, 2364. Date of birth: October 21, 1971 Position: Professor of Molecular Chemistry, Sorbonne Université, Paris E-mail: matthieu.sollogoub@sorbonne-universite.fr Homepage: http://www.ipcm.fr/presentation-665 ORCID: 0000-0003-0500-5946 Education: 1995 Master's degree, École Normale Supérieure, Université Pierre et Marie Curie, Paris 1999 PhD with Prof. Pierre Sinaÿ, Ecole Normale Supérieure 2000–2001 Postdoctoral research with Prof. Tom Brown, University of Southampton Awards: 2010 Fellow of the Institut Universitaire de France (IUF); 2011 Carbohydrate Research Award for Creativity in Carbohydrate Chemistry; 2013 Alfred Verdaguer Award, Académie des Sciences; 2018 Yoshida Lectureship Award, International Organic Chemistry Foundation (Japan) Current research interests: Organic, biological, and supramolecular glycochemistry; cyclodextrins, their functionalization and use as catalysts and molecular building blocks for supramolecular assemblies Hobbies: My family, reading, football, good wine, good food, all good things in life … My favorite molecule is glucose! So simple and yet so perfect. The secret of being a successful scientist is being able to recognize luck when it strikes. The biggest challenge facing scientists is fake news, distrust in science. Facts are not a belief! Chemistry is fun because not only do we observe and try to understand matter, but we also actively create new forms of it. Young people should study chemistry because if you don't have artistic skills, you can still become a molecular artist! Looking back over my career, I am grateful to all the fantastic students I have worked with, and for those very few but very intense moments when we realized that we were struck by luck, and sometimes that we finally achieved what we sort of planned. My favorite drink is burgundy wine, but a good Chassagne-Montrachet is a bit expensive, so a good Côtes du Rhône, Crozes-Hermitage, or Saint Joseph is perfect too, or frozen vodka with blinis, or an old whisky, or armagnac … The most important future applications of my research are unknown! My favorite quote is “Beauty will save the world” (Dostoievsky). I advise my students to make the most of their PhD time. My favorite way to spend a holiday is to go camping with my wife and our four children in southern Europe: no reservations, no plans, just nature and freedom! The principal aspect of my personality is eclecticism, maybe another word for indecision (as illustrated by my favorite books or drinks). My favorite painter is my brother Ivan Sollogoub, followed by Nicolas de Staël. My favorite musician is Leonard Cohen, a true poet, he should have had the Nobel prize with (or instead of) Bob Dylan My favorite books are The Brothers Karamazov by Dostoievsky, and also Life and Fate by Vasily Grossman—there is an amazing description on how a discovery is made by one of the characters—and Ballad of The Salt Sea by Hugo Pratt, and Jiro Taniguchi's A Distant Neighborhood. What has been you biggest influence/motivation? My father was a professor of economics at the Sorbonne, and his freedom and passion made me think that being a professor seemed like a great job. The discovery of organic chemistry at university was a revelation and the moment where you suddenly get it, you understand how it works, and how simple and beautiful it is, was key to embrace this subject. Later, at the École Normale Supérieure, I was blessed to have an amazing team of professors teaching and inspiring us: M. Julia, H. Kagan, J. Normant, P. Sinaÿ, M. Malacria, J. Livage, and C. Amatore. Then George Fleet at the University of Oxford introduced me to the beauty of carbohydrate chemistry. This love story developed into a passion during my PhD with Pierre Sinaÿ, he has had a tremendous influence on my way of doing research: to constantly be ready for the unknown, look for the real novelty, and try to do something different! What do you think the future holds for your field of research? I don't know! I hope to be surprised! Otherwise, for what is foreseeable, the development of all the dynamic aspects of chemistry, including organic and supramolecular chemistry, is probably a strongly emerging field. The study and control of temporal evolution (e.g., in situ monitoring of chemical reactivity, transport, self-assembly, operando catalysis, ageing, off-equilibrium chemistry) seems to be the way forward in molecular chemistry. As we always get inspiration from nature, it is legitimate to try to tackle the ultimate and fundamental question of life, which, from the chemist's point of view, is essentially an ensemble of out-of-equilibrium reactions and supramolecular assemblies. This is of course fascinating to study and try to understand and eventually to imitate! My 5 top papers: 1“Triisobutylaluminium and Diisobutylaluminium Hydride as Molecular Scalpels: The Regioselective Stripping of Perbenzylated Sugars and Cyclodextrins”: T. Lecourt, A. Hérault, A. J. Pearce, M. Sollogoub, P. Sinaÿ, Chem. Eur. J. 2004, 10, 2960. A turning point in my career, the discovery of a debenzylation reaction and its mechanism on sugars, and then its extension to cyclodextrins. This mechanism allowed all the subsequent work on poly-hetero-functionalization of cyclodextrins. 2“gem-Difluorocarbadisaccharides: Restoring the exo-Anomeric Effect”: B. Xu et al., Angew. Chem. Int. Ed. 2014, 53, 9597; Angew. Chem. 2014, 126, 9751. Replacing the anomeric oxygen atom or the enodocyclic one in a disaccharide to produce C-disaccharides and carbadisaccharides respectively, induces a flexibility in their interglycosidic bond, which is detrimental to their biological activity. We hypothesized that it was due to the suppression of the so-called exo-anomeric effect. To restore this effect in a carbadissacharide we added fluorine atoms, a huge synthetic effort, not obviously visible in the paper, and showed that the conformational rigidity was restored together with the exo-anomeric effect. 3“Solid-State Hierarchical Cyclodextrin-Based Supramolecular Polymer Constructed by Primary, Secondary, and Tertiary Azido Interactions”: M. Ménand, S. Adam de Beaumais, L.-M. Chamoreau, E. Derat, S. Blanchard, Y. Zhang, L. Bouteiller, M. Sollogoub, Angew. Chem. Int. Ed. 2014, 53, 7238; Angew. Chem. 2014, 126, 7366. A stroke of luck: a bis-azido-cyclodextrin was left in an NMR tube and crystalized in a hierarchical manner. This assembly has the particularity to feature both canonical forms of the azide group. Furthermore, this mode of hierarchical assembly induced by the difunctionalization of cyclodextrin inspired us for the design of the self-assembling monomer in our most recent paper in Angewandte Chemie. 4“Site-selective hexa-hetero-functionalization of α-cyclodextrin an archetypical C6-symmetric concave cycle”: B. Wang, E. Zaborova, S. Guieu, M. Petrillo, M. Guitet, Y. Blériot, M. Ménand, Y. Zhang, M. Sollogoub, Nature Comm. 2014, 5, 5354. The ultimate functionalization of α-cyclodextrin: one different function on each glucose unit. This is 1 out of 7826 ways to add up to 6 functions on a C6-symmetric concave cycle. To meet this challenge, we combined all our knowledge and reactions we developed for regioselective functionalization of cyclodextrins. This was realized as a challenge and for fun, but mainly to demonstrate that all patterns of functionality are now accessible! 5“Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration”: P. Zhang, J. Meijide Suarez, T. Driant, E. Derat, Y. Zhang, M. Ménand, S. Roland, M. Sollogoub, Angew. Chem. Int. Ed. 2017, 56, 10821; Angew. Chem. 2017, 129, 10961. Capping α- and β-cyclodextrins with an NHC ligand, both permits the encapsulation of a metal complex inside the cavity and modifies the shape of the cavity. Actually, the shapes of NHC-capped α- and β-cyclodextrins are rather different. We made use of this difference of shapes to induce an opposite regioselectivity in a copper-catalyzed hydroboration using either α- or β-cyclodextrins derivatives. Besides, when trying to rationalize this difference of selectivity, we uncovered a new reaction pathway imposed by the encapsulation of the metal and showed that not only do we have a switch in regioselectivity but also a switch of mechanism when using α- or β-cyclodextrin. Volume58, Issue7February 11, 2019Pages 1876-1877 ReferencesRelatedInformation
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