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Université Pierre et Marie Curie Paris 6,
4 Place Jussieu, 75252 Paris cedex 5

Bât F 74 2eme ét. case 181
[fr]_ Équipe GOBS
[en]_ Team GOBS

Tel:33(0)1 44 27 61 63
Fax:33(0)1 44 27 55 04


Thèmes de recherche :

Glycochimie organique, biologique et supramoléculaire

Recherche actuelle :

  • Fonctionnalisation régiosélective des cyclodextrines
  • Utilisation des cyclodextrines fonctionnelles
    • comme catalyseurs
    • pour la formation d’assemblées supramoléculaires
  • Synthèse et étude biologique de mimes de sucres

Parcours Scientifique

  • 1991-95 Etudes à l’Ecole Normale Supétieure et à l’Université de Paris 6
  • 1999 Thèse à l’Ecole Normale Supétieure et à l’Université de Paris 6 sous la direction de Pierre Sinaÿ
  • 2000-01 Stage post-doctoral à Southampton University sous la direction des Prof Tom Brown et Keith Fox
  • 2001 Maître de Conférences à l’Ecole Normale Supérieure
  • 2007 Professeur UPMC, Sorbonne Universités
  • 2010 Membre Junior de l’Institut Universitaire de France
  • 2011 Carbohydrate Research Award for Creativity
    - •2013 Prix Alfred Verdaguer de l’Institut de France, Académie des Sciences

Choix de publications :

  1. NHC-Capped Cyclodextrins (ICyDs) : Insulated Metal Complexes, Comutable Multicoordination Sphere and Cavity-Dependant Catalytisis
    M. Guitet, P. Zhang, F. Marcelo, C. Tugny, J. Jiménez-Barbero, O. Buriez, C. Amatore, V. Mouriès-Mansuy, J.-P. Goddard, L. Fensterbank, Y. Zhang, S. Roland, M. Ménand, M. Sollogoub
    Angew. Chem. Int. Ed. 2013, 52, 7213-7218
  2. An “Against-the-Rules” Double Bank Shot with Diisobutylaluminium Hydride allows Triple Functionalisation of α-Cyclodextrin
    E. Zaborova, M. Guitet, G. Prencipe, Y. Blériot, M. Ménand, M. Sollogoub
    Angew. Chem. Int. Ed. 2013, 52, 639-644
  3. Beta cyclodextrins bind, stabilize and remove lipofuscin bisretinoids from retinal pigment epithelium
    M. M. Nociari, G. L. Lehmann, A. E. Perez Bay, R. A. Radu, Z. Jiang, S. Goicochea, R. Schreiner, J. D. Warren, J. Shan, S. A. de Beaumais, M. Ménand, M Sollogoub, F. R. Maxfield, E. Rodriguez-Boulan
    Proc. Natl. Acad. Sci. U.S.A. 2014, 111, 1402-1408
  4. Primary, Secondary and Tertiary Azido Interactions build-up solid-state hierarchical Cyclodextrin-Based Supramolecular Polymer
    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, 7238-7242
  5. Gem-difluoro-carbadisaccharides : restoring the exo-anomeric effect
    B. Xu, L. Unione, J. Sardinha, S. Wu, M. Ethève-Quelquejeu, A. Pilar Rauter, Y. Blériot, Y. Zhang, S. Martín-Santamaría, D. Diaz, J. Jiménez-Barbero, M. Sollogoub
    Angew. Chem. Int. Ed. 2014, 53, 9597-9602
  6. Site-selective hexa-hetero-functionalization of -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 Comms. 2014, 5, 5354

Résultats Récents :

  • Site-selective hexa-hetero-functionalization of α-cyclodextrin an archetypical C6-symmetric concave cycle (Nature Comms. 2014, 5, 5354) Site-selective modification of symmetrical concave molecules is a highly challenging task due to the rapid increase in potential combinations as the number of sites increases. There are 7826 ways to arrange 6 beads of 6 colours on a necklace. Part of those arrangements form the background of this picture, on the forefront of which a single cyclodextrin with 6 different colours is represented. We have delineated routes to selectively functionalise six symmetrical positions, leading to a hexa-differentiated α-cyclodextrin.
  • Beta cyclodextrins bind, stabilize and remove lipofuscin bisretinoids from retinal pigment epithelium. (PNAS. 2014, 111, 1402)
  • Restoring exoanomeric effect. (Angew. Chem. Int. Ed. 2014, 53, 9597) The combination of chemical synthesis, NMR, and calculations show that it is possible to restore the anomeric effect for an acetal when replacing one of the oxygen atoms by a CF2 group. This result provides key findings in chemical sciences as it strongly suggests the importance of the stereoelectronic component for the anomeric effect. Moreover, the ability to artificially mimick the natural glycoside conformation may open new avenues for sugar-based drug design.
  • A chain is no longer than it’s weakest link. (Angew. Chem. Int. Ed. 2014, 53, 7238) The crystallization of a di-azido--cyclodextrin has revealed a polymeric self-assembly involving a rich variety of azido-type interactions. The crystal cohesion relies on the cooperativity of a primary azido inclusion, a secondary azido-azido interaction involving an unprecedented tautomeric distribution and a tertiary azido-groove interaction. The second azido group brings a major contribution to the supramolecular structure illustrating the benefit of a difunctionalization for the generation of hierarchy.
  • Don’t slam the door ! (Angew. Chem. Int. Ed. 2013, 52, 7213)

A cyclodextrin capped with a N-heterocyclic carbene allows the entrapping of a metal right in the middle of its cavity. This position induces an original set of interactions including C-H…M, C-H…X and X…π. The latter permits the closing of the cavity, which is commutable by ligand exchange. The metal appears to be very deeply buried, so as to be insulated from an electrode, but it retains activity as a catalyst. Furthermore, the cavity has an influence both on the regiochemical and the stereochemical outcome of the catalysed reactions.

  • Frustration leads to overreaction. (Angew. Chem. Int. Ed. 2013, 52, 639)

PNG - 90.7 ko

When diametrically opposed regioselective debenzylation is frustrated, an unexpected double debenzylation reaction affords original tetrafunctionalized cyclodextrins in a controlled and efficient manner.

  • You’ll never walk alone (Angew. Chem. Int. Ed., 2012, 51, 487)
    PNG - 65.1 ko

    An auto-healing process of the first host–guest complex involving a polyoxometalate hybrid and a cyclodextrin was uncovered. Indeed, this inclusion complex allows the complete restoration of the anchored organic moiety released by a basic stress, a process otherwise not fully reversible.

  • Highest TONs observed (Chem. Commun., 2011, 47, 9206)
    PNG - 68.4 ko

    Cyclodextrin-based tetraphosphine called α-Cytep glycocatalyst induces up to 340 000 000 000 TONs and 1 000 000 000 h-1 TOFs in Suzuki-Miyaura couplings.

  • Learning curve (Angew. Chem. Int. Ed., 2010, 49, 5115) img2 Regioselective twofold deprotection of benzylated cyclodextrins with diisobutylaluminum hydride affords products that can behave as enantiomers. For example, they can act as ligands for enantioselective Pd0-catalyzed reactions and their complexes display opposite circular dichroism signals (see picture). They can thus be seen as being inherently chiral cycle surrogates.