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

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

Bioorganic & medicinal chemistry (2010-10-26)
Julia Deschamp, Martine Mondon, Shinpei Nakagawa, Atsushi Kato, Dominic S Alonzi, Terry D Butters, Yongmin Zhang, Matthieu Sollogoub, Yves Blériot
ABSTRACT

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 α-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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methyl α-D-mannopyranoside, ≥99.0% (HPLC)
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