Metabolism of 24(R,S),25-epiminolanosterol to 25-aminolanosterol and lanosterol by Gibberella fujikuroi

W. David Nes, Sihua Xu, Edward J. Parish

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Mycelia of Gibberella fujikuroi metabolized 2-tritio-24(R,S),25-epiminolanosterol, a novel fungal sterol biosynthesis inhibitor that regulates Δ24-sterol methyltransferase, to 25-aminolanosterol (a new sterol) and lanosterol. The identities of the two sterols were established by cochromatography with authentic samples, mass spectroscopy, and isotopic dilution and recrystallization to constant specific activity. The newly biosynthesized tritiolanosterol was demonstrably introduced into the sterol pathway as evidenced by significant tritium label in the radiochemically purified sterols; 24(28)-methylene-24, 25-dihydrolanosterol and 14-norlanosterol. The results demonstrate for the first time the direct reduction in situ of an aziridine ring to a tertiary amine and the stereocontrolled deamination of a C-25 aminosteroid to produce a Δ24, rather than a Δ25(27), steroid.

Original languageEnglish
Pages (from-to)323-331
Number of pages9
JournalArchives of Biochemistry and Biophysics
Volume272
Issue number2
DOIs
StatePublished - Aug 1 1989

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