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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.

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 glycosi...

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Publication status:
Published

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Publisher copy:
10.1016/j.bmc.2010.09.053

Authors


Deschamp, J More by this author
Nakagawa, S More by this author
Alonzi, DS More by this author
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Journal:
Bioorganic and medicinal chemistry
Volume:
20
Issue:
2
Pages:
641-649
Publication date:
2012-01-05
DOI:
EISSN:
1464-3391
ISSN:
0968-0896
URN:
uuid:062c1db8-a4fd-4859-af0a-546383a64264
Source identifiers:
254413
Local pid:
pubs:254413

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