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Mechanism-based Enzyme Inactivators of Phytosterol Biosynthesis

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Author(s): Wenxu Zhou | Zhihong Song | Ragu Kanagasabai | Jialin Liu | Pruthvi Jayasimha | Archana Sinha | Phani Veeramachanemi | Mathew B. Miller | W. David Nes

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 4;
Start page: 185;
Date: 2004;
Original page

Keywords: Ergosterol | sitosterol | stereochemistry | sterol biosynthesis inhibitors

ABSTRACT
Current progress on the mechanism and substrate recognition by sterol methyl transferase (SMT), the role of mechanism-based inactivators, other inhibitors of SMT action to probe catalysis and phytosterol synthesis is reported. SMT is a membrane-bound enzyme which catalyzes the coupled C-methylation-deprotonation reaction of sterol acceptor molecules generating the 24-alkyl sterol side chains of fungal ergosterol and plant sitosterol. This C-methylation step can be rate-limiting in the post-lanosterol (fungal) or post-cycloartenol (plant) pathways. A series of sterol analogs designed to impair SMT activity irreversibly have provided deep insight into the C-methylation reaction and topography of the SMT active site and as reviewed provide leads for the development of antifungal agents.
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