Synthesis

Solving biological problems with Sugar mimics

  • An epoxide intermediate in glycosidase catalysis. , ACS Cent. Sci.2020, DOI : 10.1021/acscentsci.00111s
  • Fluorinated carbohydrates : Current status and perspectives, Chem. Soc. Rev.2020, accepted.
  • From 1,4-Disaccharide to 1,3-Glycosyl-Carbasugar : Synthesis of a Bespoke Inhibitor of Family GH99 Endo-α-Mannosidase, Org. Lett. 201820, 7488-7492.
  • Targetting the Pentose Phosphate Pathway : characterization of a new 6PGL inhibitor, Biophys. J. 2018115, 2114-2126.
  • Contribution of shape and charge to the inhibition of a family GH99 endo-α-1,2-mannanase, J. Am. Chem. Soc. 2017139, 1089-1097
  • Synthesis of 1,2-trans 2-acetamido-2-deoxy-homoiminosugars, Org. Lett. 201416, 5516–5519
  • Synthesis of 1,2-cis homoiminosugars derived from GlcNAc and GalNAc exploiting a β-aminoalcohol skeletal rearrangement, Org. Lett. 201416, 5512–5515
  • Gem-difluoro-carbadisaccharides : restoring the exo-anomeric effect, Angew. Chem. Int. Ed. 201453, 9597-9602
  • Non-specific accumulation of glycosphingolipids in GNE myopathy, J. Inherit. Metab. Dis. 201437, 297-308
  • Total synthesis of a sialyl Lewisx derivative for the diagnosis of cancer, Carbohydr. Res. 2014, 383, 89-96
  • Synthesis and Cytotoxicity Assay of Four Ganglioside GM3 Analogues, Eur. J. Med. Chem. 201475, 247-257
  • Efficient synthesis of chloro‐derivatives of sialosyllactosylceramide, and their enhanced inhibitory effect on epidermal growth factor receptor activation, Oncology Letters 20147, 933-940
  • Novel imino sugar -glucosidase inhibitors as antiviral compounds, Bioorg. Med. Chem. 2013, 21, 4831-4838
  • Fluoro-C-Glycosides and Fluoro-Carbasugars, Hydrolitically Stable and Synthetically Challenging GlycomimeticsChem. Soc. Rev2013, doi:10.1039/C2CS35403A
  • Efficient access to peptidyl-RNA conjugates for picomolar inhibition of non-ribosomal FemXWv aminoacyl-transferase, Chem. Eur. J. 201319, 1357 – 1363
  • Synthesis and conformational analysis of bicyclic mimics of α and -β-D-glucopyranosides adopting the biologically relevant 2,5B conformation Carbohydr. Res. 2012361, 219–224
  • Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling, New J. Chem.201236, 1008-1013
  • Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors, Carbohydr. Res2012356, 110-114
  • Towards a stable noeuromycin analog with a D-manno configuration : Synthesis and glycosidase inhibition of D-manno-like tri- and tetrahydroxylated Azepanes,Bioorg. Med. Chem.201220, 641–649
  • Analogues de nucleosides pour le traitement d’une infection virale, demande de brevet FR 1159622 du 24 octobre 2011
  • Imino-Sugar C-Glycosides, Preparation and Use Thereof, EP 11305942.2, 20 July 2011
  • Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chainOrg. Biomol. Chem., 2011, 9, 5373-5388
  • Direct experimental evidence for the high chemical reactivity of α- and β- xylopyranosides adopting a 2,5B conformation in glycosyl transfer, Chem. Eur. J.201117, 7345-7356 L. Amorim, F. Marcelo, C. Rousseau, L. Nieto, J. Jiménez-Barbero, J. Marrot, A. P. Rauter, M. Sollogoub, M. Bols, Y. Blériot
  • Analysis of the reaction coordinate of α–L fucosidases : a combined structural and quantum mechanical approach, J. Am. Chem. Soc.2010132, 1804-1806
  • Molecular Basis for Inhibition of GH84 Glycoside Hydrolases by Substituted Azepanes : Conformational Flexibility Enables Probing of Substrate Distortion, J. Am. Chem. Soc.2009131, 5390–5392
  • Design and synthesis of acetamido tri- and tetra-hydroxyazepanes : potent and selective β-N-acetylhexosaminidase inhibitors, Bioorg. Med. Chem. 200917, 5598-5604
  • Hemi-Carbasucrose : Turning off exoanomeric effect induces less flexibility, Chem. Asian J. 20083, 51-58
  • Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics, Chem. Eur. J. 2008, 14, 10066-10073
  • First Synthesis of 5-Fluoro-(+)-MK7607, its 1-Epimer and 6-Deoxy Derivative, Tetrahedron Lett.200849, 5548-5550
  • Transition-state mimicry in mannoside hydrolysis : characterisation of twenty-six inhibitors and insight into binding from linear free energy relationships and 3-D structure, Nat. Chem. Biol. 20084, 306-312
  • Phenylenediamine catalysis of “click glycosylations” in water : practical and direct access to unprotected neoglycoconjugates Org. Biomol. Chem., 20086, 1898-1901
  • New Synthetic Seven-Membered 1-Azasugars Displaying Potent Inhibition Towards Glycosidases and Glucosylceramide Transferase, ChemBioChem 20089, 253-260
  • gem-Difluorocarbasugars, the cases of mannose and galactose, Carbohydr. Res. 2007342, 1689-1703
  • Tandem Staudinger–azaWittig mediated ring expansion : rapid access to new isofagomine-tetrahydroxyazepane hybrids, Chem. Commun.2007, 183-185
  • Alkylalanes and methyl furanosides : regioselective de-O-benzylation or acetal cleavage, Carbohydr. Res. 2006341, 2135-3144
  • Pd-catalysed Capping Removal on a Tri-differentiated α -CyclodextrinChem. Lett.200635, 534-535
  • The First Synthesis of gem-Difluoro-Carba-D-Glucose, a Step Further in Sugar Mimesis, Angew. Chem., Int. Ed. Engl.2004, 43, 6680-6683
  • The first synthesis of substituted azepanes mimicking monosaccharides : a new class of potent glycosidase inhibitors, Org. Biomol. Chem., 20042, 1492-1499
  • Trimethylaluminium (TMAL) promoted rearrangements of unsaturated sugars into cyclohexanes, Tetrahedron : Asymm.200415, 699-703
  • Diisobutylaluminium hydride (DIBAL-H) as a molecular scalpel : a new mechanistic proposal for a spiroketal rearrangement, Tetrahedron Lett. 200445, 8165-8168
  • Triisobutylaluminium and diisobutylaluminium hydride as molecular scalpels : the regioselective stripping of perbenzylated sugars and cyclodextrins, Chem. Eur. J.200410, 2960-2971

 

  • Cycloheptanic sugar mimetics, bridging the gap in the homologous series of carbocyclic analogues, Tetrahedron, 200258, 10189-10196
  • From Glucose to Cyclooctanic Carba-glucose : a New Class of Carbohydrate Mimetics, Angew. Chem., Int. Ed. Engl.200039, 2466-2467
  • Carbocyclic Ring Closure of Unsaturated S-, Se– and C– Aryl Glycosides, Angew. Chem., Int. Ed. Engl.200039, 362-364