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Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease

Abstract:

A series of iminosugars bearing two or three alkyl chains ('iminoglycolipids') were designed as ceramide mimics and analogues of N-butyl 1-deoxynojirimycin (N-Bu DNJ, Zavesca®). This orally active iminosugar inhibits the biosynthesis of glucosylceramides, which accumulate pathologically in macrophages of patients with Gaucher disease (substrate reduction therapy, SRT). Molecular modeling and kinetic experiments have suggested that N-Bu DNJ is a competitive inhibitor that mimics the ceramide a...

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Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
16
Issue:
10
Pages:
1747-1756
Publication date:
2005-05-23
DOI:
ISSN:
0957-4166
URN:
uuid:dfa731f9-d32d-47b6-8d8d-1dbaaae53e16
Source identifiers:
101005
Local pid:
pubs:101005
Language:
English

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