Alteration of the substrate's prefolded conformation and cyclization stereochemistry of oxidosqualene-lanosterol cyclase of saccharomyces cerevisiae by substitution at Phenylalanine 699

Tung-Kung Wu*, Cheng Hsiang Chang, Hao Yu Wen, Yuan Ting Liu, Wen Hsuan Li, Tsai Ting Wang, Wen Shiang Shie

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

[Chemical equaction presented] The Saccharomyces cerevisiae ERG7 Phe699 mutants produced one chair-chair-chair (C-C-C) and two chair-boat-chair (C-B-C) truncated tricyclic compounds, one tetracyclic 17α-exocyclic unrearranged intermediate, and two 17β-exocyclic truncated rearranged intermediates. These results provided direct evidence for the importance of the residue In affecting mechanistic transitions between C-B-C and C-C-C substrate conformation and between the 17α- and 17β-exocyclic side chain stereochemistry as well as in stabilizing the 6-6-5 tricyclic and the protosteryl C-17 cations.

Original languageEnglish
Pages (from-to)500-503
Number of pages4
JournalOrganic Letters
Volume12
Issue number3
DOIs
StatePublished - 5 Feb 2010

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