Sterol methyl transferase. Evidence for successive C-methyl transfer reactions generating Δ24(28)- and Δ25(27)-olefins by a single plant enzyme

Allen L. Dennis, W. David Nes

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The native SMT from Glycine max (soybean) expressed in Escherichia coli cells catalyzes the step-wise conversion of cycloartenol to 24(28)-methylene cycloartanol to a mixture of stereochemically related Δ24(28)Z-ethylidene-Δ24(28)E-ethylidene- and Δ25(27)-24β-ethylcyclosterols. [27-13C]Cycloartenol was tested as a substrate to determine the C-25 configuration of the Δ24(28)-olefin formed during the first C1-transfer reaction. This substrate yielded (25-R)-[27-13C]24(28)-methylenecycloartanol. These results are entirely consistent with the observed stereochemistries of pathway specific 24-alkyl sterols found in plants and additionally revealed for the first time that a SMT can sequentially C-methylate the Δ24-bond to generate multiple olefins.

Original languageEnglish
Pages (from-to)7017-7021
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number39
DOIs
StatePublished - Sep 23 2002

Keywords

  • Cycloartenol
  • Methyl transferase
  • Phytosterol
  • Sitosterol
  • Soybean
  • Stereochemistry
  • Sterol

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