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Désiré J, Foucart Q, Poveda A, et al. Synthesis, conformational analysis and glycosidase inhibition of bicyclic nojirimycin C-glycosides based on an octahydrofuro[3,2-b]pyridine motif. Carbohydr Res. 2021;511:108491doi: 10.1016/j.carres.2021.108491.
Désiré, J., Foucart, Q., Poveda, A., Gourlaouen, G., Shimadate, Y., Kise, M., Proceviat, C., Ashmus, R., Vocadlo, D. J., Jiménez-Barbero, J., Kato, A., & Blériot, Y. (2021). Synthesis, conformational analysis and glycosidase inhibition of bicyclic nojirimycin C-glycosides based on an octahydrofuro[3,2-b]pyridine motif. Carbohydrate research, 511108491. https://doi.org/10.1016/j.carres.2021.108491
Désiré, Jérôme, et al. "Synthesis, conformational analysis and glycosidase inhibition of bicyclic nojirimycin C-glycosides based on an octahydrofuro[3,2-b]pyridine motif." Carbohydrate research vol. 511 (2021): 108491. doi: https://doi.org/10.1016/j.carres.2021.108491
Désiré J, Foucart Q, Poveda A, Gourlaouen G, Shimadate Y, Kise M, Proceviat C, Ashmus R, Vocadlo DJ, Jiménez-Barbero J, Kato A, Blériot Y. Synthesis, conformational analysis and glycosidase inhibition of bicyclic nojirimycin C-glycosides based on an octahydrofuro[3,2-b]pyridine motif. Carbohydr Res. 2021 Dec 20;511:108491. doi: 10.1016/j.carres.2021.108491. Epub 2021 Dec 20. PMID: 34953389.
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Carbohydr Res. 2021 Dec 20;511:108491. doi: 10.1016/j.carres.2021.108491. Epub 2021 Dec 20.

Synthesis, conformational analysis and glycosidase inhibition of bicyclic nojirimycin C-glycosides based on an octahydrofuro[3,2-b]pyridine motif.

Carbohydrate research

Jérôme Désiré, Quentin Foucart, Ana Poveda, Gurvan Gourlaouen, Yuna Shimadate, Maki Kise, Cameron Proceviat, Roger Ashmus, David J Vocadlo, Jesús Jiménez-Barbero, Atsushi Kato, Yves Blériot

Affiliations

  1. Université de Poitiers, IC2MP, UMR CNRS 7285, Equipe "Synthèse Organique", Groupe Glycochimie, 4 rue Michel Brunet, 86073, Poitiers Cedex 9, France. Electronic address: [email protected].
  2. Université de Poitiers, IC2MP, UMR CNRS 7285, Equipe "Synthèse Organique", Groupe Glycochimie, 4 rue Michel Brunet, 86073, Poitiers Cedex 9, France.
  3. CIC bioGUNE, Parque technologico de Bizkaia, Edif. 801A-1°, Derio-Bizkaia 48160, and Ikerbasque, Basque Foundation for Science, Maria Lopez de Haro 3, 48013, Bilbao, Spain.
  4. Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan.
  5. Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada, V5S 1P6.
  6. Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan. Electronic address: [email protected].
  7. Université de Poitiers, IC2MP, UMR CNRS 7285, Equipe "Synthèse Organique", Groupe Glycochimie, 4 rue Michel Brunet, 86073, Poitiers Cedex 9, France. Electronic address: [email protected].

PMID: 34953389 DOI: 10.1016/j.carres.2021.108491

Abstract

A set of bicyclic iminosugar C-glycosides, based on an octahydrofuro[3,2-b]pyridine motif, has been synthesized from a C-allyl iminosugar exploiting a debenzylative iodocycloetherification and an iodine nucleophilic displacement as the key steps. The halogen allowed the introduction of a range of aglycon moieties of different sizes bearing several functionalities such as alcohol, amine, amide and triazole. In these carbohydrate mimics the fused THF ring forces the piperidine to adopt a flattened

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Keywords: Bicycle; Conformation; Glycosidase; Hexosaminidase; Iminosugar; Inhibition

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