The Enzyme Database

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EC 1.14.14.49     
Accepted name: 12-hydroxyjasmonoyl-L-amino acid 12-hydroxylase
Reaction: a 12-hydroxyjasmonoyl-L-amino acid + 2 [reduced NADPH—hemoprotein reductase] + 2 O2 = a 12-hydroxy-12-oxojasmonoyl-L-amino acid + 2 [oxidized NADPH—hemoprotein reductase] + 3 H2O (overall reaction)
(1a) a 12-hydroxyjasmonoyl-L-amino acid + [reduced NADPH—hemoprotein reductase] + O2 = a 12-oxojasmonoyl-L-amino acid + [oxidized NADPH—hemoprotein reductase] + 2 H2O
(1b) a 12-oxojasmonoyl-L-amino acid + [reduced NADPH—hemoprotein reductase] + O2 = a 12-hydroxy-12-oxojasmonoyl-L-amino acid + [oxidized NADPH—hemoprotein reductase] + H2O
Glossary: 12-hydroxy-12-oxojasmonate = (3Z)-5-[(1R,2R)-2-(carboxymethyl)-5-oxocyclopentyl]pent-3-enoate
Other name(s): CYP94C1 (gene name)
Systematic name: 12-hydroxyjasmonoyl-L-amino acid,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (12-hydroxylating)
Comments: A cytochrome P450 (heme thiolate) enzyme found in plants. The enzyme acts on jasmonoyl-L-amino acid conjugates that have been hydroxylated at the C-12 position of jasmonic acid by EC 1.14.14.48, jasmonoyl-L-amino acid 12-hydroxylase, further oxidizing that position to a carboxylate via an aldehyde intermediate. While the best studied substrate is (+)-7-epi-jasmonoyl-L-isoleucine, the enzyme was shown to be active with jasmonoyl-L-phenylalanine, and is likely to be active with other jasmonoyl-amino acid conjugates.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Heitz, T., Widemann, E., Lugan, R., Miesch, L., Ullmann, P., Desaubry, L., Holder, E., Grausem, B., Kandel, S., Miesch, M., Werck-Reichhart, D. and Pinot, F. Cytochromes P450 CYP94C1 and CYP94B3 catalyze two successive oxidation steps of plant hormone jasmonoyl-isoleucine for catabolic turnover. J. Biol. Chem. 287 (2012) 6296–6306. [PMID: 22215670]
2.  Widemann, E., Grausem, B., Renault, H., Pineau, E., Heinrich, C., Lugan, R., Ullmann, P., Miesch, L., Aubert, Y., Miesch, M., Heitz, T. and Pinot, F. Sequential oxidation of jasmonoyl-phenylalanine and jasmonoyl-isoleucine by multiple cytochrome P450 of the CYP94 family through newly identified aldehyde intermediates. Phytochemistry 117 (2015) 388–399. [PMID: 26164240]
3.  Bruckhoff, V., Haroth, S., Feussner, K., Konig, S., Brodhun, F. and Feussner, I. Functional characterization of CYP94-genes and identification of a novel jasmonate catabolite in flowers. PLoS One 11 (2016) e0159875. [PMID: 27459369]
[EC 1.14.14.49 created 2017]
 
 


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