Abstract
The rationally designed substrate mimic of cycloartenol, 24-thiacycloartanol (24-TC) 4A , and its corresponding sulfonium salt 5A were tested against the recombinant sterol methyltransferase (SMT) from Glycine max (soybean). Analog 4A was found to irreversibly inactivate the enzyme generating competitive- and time-dependent inhibition of activity accompanied by a K i value of 2 μM and k inact of 0.3 min −1. Analog 5A , a presumptive high-energy intermediate of the SMT catalyzed reaction, was found to be a reversible, non-competitive-type inhibitor generating a K i value of 55 nM.
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