Differential stereocontrolled formation of tricyclic triterpenes by mutation of tyrosine 99 of the oxidosqualene-lanosterol cyclase from saccharomyces cerevisiae

Tung-Kung Wu*, Wen Hsuan Li, Cheng Hsiang Chang, Hao Yu Wen, Yuan Ting Liu, Yi Chun Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

The function of the Tyr99 residue from Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase (ERG7) was analyzed by constructing deletion, and site-saturated mutants. Two truncated intermediates, (13αH)- isomalabarica-14Z,17E,21-trien-3βol and. (13α\H)-isomalabarica-14Z, 17.E,21.-trien-3β-ol, were isolated from the ERG7Y99X mutants. These results suggest that the functional role of ERG7Y99 is to affect both chair-boat 6-65 tricyclic Markovnikov C-14 cation stabilization and the stereochemistry of the protons at the C-15 position for subsequent deprotonation.

Original languageEnglish
Pages (from-to)5731-5737
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number33
DOIs
StatePublished - 1 Dec 2009

Keywords

  • Cyclization
  • Enzymes
  • Mutagenesis
  • Reaction mechanisms
  • Terpenoids

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