Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 7, Pages 1627-1636Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801578
Keywords
enzyme structures; maltase glucoamylase; natural products; total synthesis; trehalase
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Funding
- NSERC Canada
- CIHR [MOP79400]
- Heart and Stroke Canada [NA-6305]
- BBSRC
- Royal Society/Wolfson Research Merit award
- Sir Henry Wellcome postdoctoral fellow
- Cornell High Energy Synchrotron Source (CHESS)
- National Science Foundation [DMR-0225180]
- Macromolecular Diffraction at CHESS (MacCHESS)
- National Institutes of Health [RR-01646]
- National Center for Research Resources
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Total synthesis of naturally occurring casuarine (1) and the first total synthesis of casuarine 6-O-alpha-glucoside (2) were achieved through complete stereoselective nitrone cycloaddition, Tamao-Fleming oxidation and selective alpha-glucosylation as key steps. Biological assays of the two compounds proved their strong and selective inhibitory properties towards glucoamylase NtMGAM and trehalase Tre37A, respectively, which place them among the most powerful inhibitors of these enzymes. The structural determination of the complexes of NtMGAM with 1 and of Tre37A with 2 revealed interesting similarities in the catalytic sites of these two enzymes which belong to different families and clans.
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