Fluorinated carbohydrates as chemical probes for molecular recognition studies. Current status and perspectives
This review provides an extensive summary of the effects of carbohydrate fluorination with regard to changes in physical, chemical and biological properties with respect to regular saccharides. The specific structural, conformational, stability, reactivity and interaction features of fluorinated sug...
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| Published in | Chemical Society reviews Vol. 49; no. 12; pp. 3863 - 3888 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
22.06.2020
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| Subjects | |
| Online Access | Get full text |
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| Summary: | This review provides an extensive summary of the effects of carbohydrate fluorination with regard to changes in physical, chemical and biological properties with respect to regular saccharides. The specific structural, conformational, stability, reactivity and interaction features of fluorinated sugars are described, as well as their applications as probes and in chemical biology.
Fluorinated carbohydrates have become indispensable in glycosciences. This contribution provides an overview of how fluorine introduction modifies physical and chemical properties of carbohydrates along with selected examples of its applications. |
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| Bibliography: | Bruno Linclau is Professor of Organic Chemistry at School of Chemistry, University of Southampton. He earned his Licentiate in Sciences (Chemistry) degree from the University of Ghent (Belgium), where he also obtained his PhD in 1996 with Prof. Maurits Vandewalle. He carried out postdoctoral research with Professor Dennis P. Curran at the University of Pittsburgh, Pittsburgh PA (USA) with a fellowship from the Belgian American Educational Foundation. He joined the faculty at Southampton University in 1999. Ana Ardá studied Chemistry at the University of A Coruña, from where she received her doctorate in Chemistry in 2006. Between 2006 and 2008 she carried out a postdoctoral stay in at Utrecht University, with Prof. Hans Kamerling where she started to work with carbohydrates. In 2008 she moved to Centro de Investigaciones Biológicas (CIB-CSIC) in Madrid to join Prof. Jiménez-Barbero's group. In 2014 she moved to CIC bioGUNE in the Basque Country, and since December 2015 she is a Ramón y Cajal Fellow. Her research interests are focused on the study of glycan-protein interactions through a multidisciplinary approach, with a special focus on NMR techniques. Niels Reichardt is group leader at CIC biomaGUNE. He received his PhD in Chemistry from Konstanz University, Germany. His postgraduate studies on projects in synthetic carbohydrate chemistry were carried out at the Institute for Chemical Research of the CSIC in Seville. After a short postdoctoral stay with Professor Nicola Winnsinger at the University Luis Pasteur, Strasbourg, he moved to industry to work as a Research Scientist for Glycoform Ltd, Oxford, developing synthetic therapeutic glycoproteins until 2006. In 2006, he became group leader for glycotechnology at CIC biomaGUNE in San Sebastian. His current research interests include the synthesis of oligosaccharides and glycomimetics of biological interest, array-based functional glycomics and the development of quantitative glycan profiling methods for biotechnology and diagnostics. Luca Unione studied Chemistry at the University of Napoli Federico II (Italy). He received the PhD in 2016 in Madrid (Spain), in the framework of the ITN-Marie Sk odowska-Curie, working in the field of structural characterization of carbohydrates, glycomimetics and their interactions with glycan binding proteins. He carried out a postdoctoral stay in the company Atlas molecular Pharma founded by the Center for Cooperative Research in Bioscience (CIC bioGUNE) in Biscay (Spain). The main aim of the company is to discover first-in-class, innovative therapeutics for the treatment of Rare and Ultra-Rare Diseases. In 2019 he moved to Utrecht University (The Netherlands) as postdoctoral fellow under the International Human Frontier Science Program (HFSP). His research interest is focused on the understanding of the role of glycans as regulators in biomedical processes, with a special focus on chemo-enzymatic synthesis of glycans and the study of glycan-protein interactions through a multidisciplinary approach. Jesús Jiménez-Barbero is Ikerbasque Research Professor and Scientific Director of CIC bioGUNE since 2014. He received his PhD in 1987 at Madrid. After postdoctoral stays at Zürich, Mill Hill, and Pittsburgh, he returned to Madrid (CSIC) and started to work on protein-carbohydrate interactions. In 2002 he was promoted to CSIC Research Professor at CIB, where he developed his scientific activity until he moved to Bilbao. His scientific interest is focused in the field of molecular recognition and Chemical Glycobiology, employing a multidisciplinary approach that combines synthesis, biochemistry, molecular biology, molecular modeling, and especially NMR, enjoying a wide network of scientific collaborations worldwide. Stéphane Vincent received his Master and PhD degrees in bioorganic chemistry from the Université Louis Pasteur (Strasbourg, France) with Professor Charles Mioskowski. After postdoctoral studies first at The Scripps Research Institute in the research group of Professor Chi-Huey Wong and then in Strasbourg with Prof. Jean-Marie Lehn, he took up a permanent position as a CNRS researcher in 2001 at the Ecole Normale Supérieure (Paris). In 2004, he began an appointment at Université de Namur (Belgium), as Assistant Professor and then, Full Professor in 2014. His research interests include the glycosciences, biocatalysis, and mechanistic enzymology. Matthieu Sollogoub is Professor of Molecular Chemistry at Sorbonne University where he conducts his research team on various aspects of carbohydrate chemistry. He focuses mainly on cyclodextrin functionalization for catalysis and supramolecular assembly, he also explores carbohydrate mimickry. He obtained his PhD at the Ecole Normale Supérieure (ENS) in Paris in 1999 with Prof. P. Sinaÿ. He carried out postdoctoral research at the University of Southampton with Prof. T. Brown and joined the faculty of ENS and Sorbonne in 2001. In 2011, he received the Carbohydrate Research Award for Creativity in Glycoscience. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
| ISSN: | 0306-0012 1460-4744 1460-4744 |
| DOI: | 10.1039/c9cs00099b |