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Synthesis and Structural Revision of Glyphaeaside C
Brendan J Byatt1, Atsushi Kato2, Stephen G Pyne1
1School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia.
Abstract:
The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.
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