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Chemical Compound Review:

AGN-PC-00D591 N-[2-(1H-indol-3- yl)ethylidene]hydroxylamine

Synonyms: AG-A-50480, ACMC-20lzrt, CTK1A3420, CTK3F3840, AC1L986B, ...

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Disease relevance of C05836

The cytochrome P450 CYP79B1 from Sinapis alba has been heterologously expressed in Escherichia coli and shown to catalyze the conversion of tryptophan to indole-3-acetaldoxime [1].

High impact information on C05836

Here we provide in planta evidence that the two Arabidopsis cytochrome P450s, CYP79B2 and CYP79B3, which convert tryptophan (Trp) to indole-3-acetaldoxime (IAOx) in vitro, are critical enzymes in auxin biosynthesis in vivo [2].
CYP83B1 N-hydroxylates indole-3-acetaldoxime to the corresponding aci-nitro compound, 1-aci-nitro-2-indolyl-ethane, with a K(m) of 3 microM and a turnover number of 53 min(-1) [3].
We show that camalexin, the indole phytoalexin of Arabidopsis thaliana, is synthesized from tryptophan via indole-3-acetaldoxime (IAOx) in a reaction catalyzed by CYP79B2 and CYP79B3 [4].
Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis [4].
Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid [5].

Biological context of C05836

Probing crucial metabolic pathways in fungal pathogens of crucifers: biotransformation of indole-3-acetaldoxime, 4-hydroxyphenylacetaldoxime, and their metabolites [6].

Associations of C05836 with other chemical compounds

In Arabidopsis thaliana, indole-3-acetaldoxime (IAOx) produced from tryptophan by the activity of two cytochrome P450 enzymes, CYP79B2 and CYP79B3, serves as a precursor for IGS biosynthesis but is also an intermediate in the biosynthetic pathway of indole-3-acetic acid (IAA) [7].
As well, the antifungal activity of indole-3-acetaldoxime and metabolites and the synthesis and biotransformation of 4-hydroxyphenylacetaldoxime by the same plant pathogens and by an insect fungal pathogen, Beauveria bassiana, are reported [6].
The metabolism of the cruciferous phytoalexins brassinin and cyclobrassinin, and the related compounds indole-3-carboxaldehyde, glucobrassicin, and indole-3-acetaldoxime was investigated in various plant tissues of Brassica juncea and B. rapa [8].

Gene context of C05836

However, indole-3-acetaldoxime has a 50-fold higher affinity toward CYP83B1 than toward CYP83A1 [9].

References

CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime. Naur, P., Hansen, C.H., Bak, S., Hansen, B.G., Jensen, N.B., Nielsen, H.L., Halkier, B.A. Arch. Biochem. Biophys. (2003) [Pubmed]
Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Zhao, Y., Hull, A.K., Gupta, N.R., Goss, K.A., Alonso, J., Ecker, J.R., Normanly, J., Chory, J., Celenza, J.L. Genes Dev. (2002) [Pubmed]
CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis. Bak, S., Tax, F.E., Feldmann, K.A., Galbraith, D.W., Feyereisen, R. Plant Cell (2001) [Pubmed]
Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis. Glawischnig, E., Hansen, B.G., Olsen, C.E., Halkier, B.A. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid. Mikkelsen, M.D., Hansen, C.H., Wittstock, U., Halkier, B.A. J. Biol. Chem. (2000) [Pubmed]
Probing crucial metabolic pathways in fungal pathogens of crucifers: biotransformation of indole-3-acetaldoxime, 4-hydroxyphenylacetaldoxime, and their metabolites. Pedras, M.S., Montaut, S. Bioorg. Med. Chem. (2003) [Pubmed]
DOF transcription factor AtDof1.1 (OBP2) is part of a regulatory network controlling glucosinolate biosynthesis in Arabidopsis. Skirycz, A., Reichelt, M., Burow, M., Birkemeyer, C., Rolcik, J., Kopka, J., Zanor, M.I., Gershenzon, J., Strnad, M., Szopa, J., Mueller-Roeber, B., Witt, I. Plant J. (2006) [Pubmed]
Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Pedras, M.S., Nycholat, C.M., Montaut, S., Xu, Y., Khan, A.Q. Phytochemistry (2002) [Pubmed]
The involvement of two p450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis. Bak, S., Feyereisen, R. Plant Physiol. (2001) [Pubmed]

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