CYP83B1 is the oxime-metabolizing enzyme in the glucosinolate pathway in Arabidopsis

被引:129
作者
Hansen, CH
Du, LC
Naur, P
Olsen, CE
Axelsen, KB
Hick, AJ
Pickett, JA
Halkier, BA
机构
[1] Royal Vet & Agr Univ, Plant Biochem Lab, DK-1871 Frederiksberg C, Denmark
[2] Royal Vet & Agr Univ, Dept Chem, DK-1871 Frederiksberg, Denmark
[3] Royal Vet & Agr Univ, Ctr Mol Plant Physiol, DK-1871 Frederiksberg C, Denmark
[4] Swiss Inst Bioinformat, SwissProt Grp, CH-1211 Geneva 4, Switzerland
[5] IACR Rothamsted, Harpenden AL5 2JQ, Herts, England
关键词
D O I
10.1074/jbc.M102637200
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
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页码:24790 / 24796
页数:7
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