Towards a stable noeuromycin analog with a D-manno configuration: Synthesis and glycosidase inhibition of D-manno-like tri- and tetrahydroxylated azepanes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Bioorganic and Medicinal Chemistry Année : 2012

Towards a stable noeuromycin analog with a D-manno configuration: Synthesis and glycosidase inhibition of D-manno-like tri- and tetrahydroxylated azepanes

Résumé

Noeuromycin is a highly potent albeit unstable glycosidase inhibitor due to its hemiaminal function. While stable D-gluco-like analogs have been reported, no data are available for D-manno-like structures. A series of tri- and tetrahydroxylated seven-membered iminosugars displaying either a D-manno-or a L-gulo-like configuration, were synthesized from methyl alpha-D-mannopyranoside using a reductive amination-mediated ring expansion as the key step. Screening towards a range of commercial glycosidases demonstrated their potency as competitive glycosidase inhibitors while cellular assay showed selective albeit weak glycoprotein processing mannosidase inactivation.

Dates et versions

hal-00836749 , version 1 (21-06-2013)

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Citer

J. Deschamp, M. Mondon, S. Nakagawa, S. Kato, D.S. Alonzi, et al.. Towards a stable noeuromycin analog with a D-manno configuration: Synthesis and glycosidase inhibition of D-manno-like tri- and tetrahydroxylated azepanes. Bioorganic and Medicinal Chemistry, 2012, 20 (2), pp.641-649. ⟨10.1016/j.bmc.2010.09.053⟩. ⟨hal-00836749⟩
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