CYP83B1 Is the Oxime-metabolizing Enzyme in the Glucosinolate Pathway in Arabidopsis

Carsten Hørslev Hansen, Liangcheng Du, Peter Naur, Carl Erik Olsen, Kristian B. Axelsen, Alastair J. Hick, John A. Pickett, Barbara Ann Halkier

Research output: Contribution to journalArticle

116 Scopus citations

Abstract

CYP83B1 from Arabidopsis thaliana has been identified as the oxime-metabolizing enzyme in the biosynthetic pathway of glucosinolates. Biosynthetically active microsomes isolated from Sinapis alba converted p-hydroxyphenylacetaldoxime and cysteine into S-alkylated p-hydroxyphenylacetothiohydroximate, S-(p-hydroxyphenylacetohydroximoyl)-L-cysteine, the next proposed intermediate in the glucosinolate pathway. The production was shown to be dependent on a cytochrome P450 monooxygenase. We searched the genome of A. thaliana for homologues of CYP71E1 (P450ox), the only known oxime-metabolizing enzyme in the biosynthetic pathway of the evolutionarily related cyanogenic glucosides. By a combined use of bioinformatics, published expression data, and knock-out phenotypes, we identified the cytochrome P450 CYP83B1 as the oxime-metabolizing enzyme in the glucosinolate pathway as evidenced by characterization of the recombinant protein expressed in Escherichia coli. The data are consistent with the hypothesis that the oxime-metabolizing enzyme in the cyanogenic pathway (P450ox) was mutated into a "P450mox" that converted oximes into toxic compounds that the plant detoxified into glucosinolates.

Original languageEnglish (US)
Pages (from-to)24790-24796
Number of pages7
JournalJournal of Biological Chemistry
Volume276
Issue number27
DOIs
StatePublished - Jul 6 2001

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Cell Biology

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    Hansen, C. H., Du, L., Naur, P., Olsen, C. E., Axelsen, K. B., Hick, A. J., Pickett, J. A., & Halkier, B. A. (2001). CYP83B1 Is the Oxime-metabolizing Enzyme in the Glucosinolate Pathway in Arabidopsis. Journal of Biological Chemistry, 276(27), 24790-24796. https://doi.org/10.1074/jbc.M102637200