24-Thiacycloartanol, a potent mechanism-based inactivator of plant sterol methyltransferase

Wenxu Zhou, Zhihong Song, Jialin Liu, Matthew B. Miller, W. David Nes

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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 2μM and kinact of 0.3min-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 Ki value of 55nM.

Original languageEnglish
Pages (from-to)875-878
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number4
DOIs
StatePublished - Jan 19 2004

Keywords

  • Enzymology
  • Mechanism-based inhibitor
  • Phytosterol
  • Sterol methyltransferase

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