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J Biol Chem, Vol. 275, Issue 19, 14659-14666, May 12, 2000
From the Plant Biochemistry Laboratory, Department of Plant
Biology, and Center for Molecular Plant Physiology (PlaCe), The Royal
Veterinary and Agricultural University, Thorvaldsensvej 40, DK-1871
Frederiksberg C, Copenhagen, Denmark
Glucosinolates are natural plant products gaining
increasing interest as cancer-preventing agents and crop protectants.
Similar to cyanogenic glucosides, glucosinolates are derived from amino acids and have aldoximes as intermediates. We report cloning and characterization of cytochrome P450 CYP79A2 involved in aldoxime formation in the glucosinolate-producing Arabidopsis
thaliana L. The CYP79A2 cDNA was cloned by polymerase chain
reaction, and CYP79A2 was functionally expressed in Escherichia
coli. Characterization of the recombinant protein shows that
CYP79A2 is an N-hydroxylase converting
L-phenylalanine into phenylacetaldoxime, the precursor of
benzylglucosinolate. Transgenic A. thaliana constitutively expressing CYP79A2 accumulate high levels of benzylglucosinolate. CYP79A2 expressed in E. coli has a Km
of 6.7 µmol liter The nucleotide sequence(s) reported in this paper has been submitted to the GenBankTM/EMBL Data Bank with accession number(s) AF245302.
Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the Conversion of L-Phenylalanine to
Phenylacetaldoxime in the Biosynthesis of Benzylglucosinolate*
1 for L-phenylalanine.
Neither L-tyrosine, L-tryptophan,
L-methionine, nor DL-homophenylalanine are
metabolized by CYP79A2, indicating that the enzyme has a narrow
substrate specificity. CYP79A2 is the first enzyme shown to catalyze
the conversion of an amino acid to the aldoxime in the biosynthesis of
glucosinolates. Our data provide the first conclusive evidence that
evolutionarily conserved cytochromes P450 catalyze this step common for
the biosynthetic pathways of glucosinolates and cyanogenic glucosides.
This strongly indicates that the biosynthesis of glucosinolates has
evolved based on a cyanogenic predisposition.
*
This work was supported by the Danish National Research
Foundation.The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in
accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
To whom correspondence should be addressed. Tel.: 45-35283342;
Fax: 45-35283333; E-mail: halkier@biobase.dk.
Copyright © 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
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