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SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor

View ORCID ProfileVeronica C. Perez, View ORCID ProfileRu Dai, Breanna Tomiczek, View ORCID ProfileJorrel Mendoza, View ORCID ProfileEmily S.A. Wolf, Alexander Grenning, View ORCID ProfileWilfred Vermerris, View ORCID ProfileAnna K. Block, View ORCID ProfileJeongim Kim
doi: https://doi.org/10.1101/2022.05.11.491506
Veronica C. Perez
5Plant Molecular and Cellular Biology Program, University of Florida, FL, 32611
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Ru Dai
1Horticultural Sciences Department, University of Florida, Gainesville, FL, 32611
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Breanna Tomiczek
4Department of Chemistry, University of Florida, Gainesville, FL, 32611
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Jorrel Mendoza
3Chemistry Research Unit, Center for Medical, Agricultural and Veterinary Entomology, U.S. Department of Agriculture-Agricultural Research Service, Gainesville, FL, 32608
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Emily S.A. Wolf
5Plant Molecular and Cellular Biology Program, University of Florida, FL, 32611
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Alexander Grenning
4Department of Chemistry, University of Florida, Gainesville, FL, 32611
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Wilfred Vermerris
2Department of Microbiology & Cell Science, Gainesville, FL, 32611
5Plant Molecular and Cellular Biology Program, University of Florida, FL, 32611
6UF Genetics Institute, University of Florida, FL, 32611
7Florida Center for Renewable Chemicals and Fuels, University of Florida, FL, 32611
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Anna K. Block
3Chemistry Research Unit, Center for Medical, Agricultural and Veterinary Entomology, U.S. Department of Agriculture-Agricultural Research Service, Gainesville, FL, 32608
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Jeongim Kim
1Horticultural Sciences Department, University of Florida, Gainesville, FL, 32611
5Plant Molecular and Cellular Biology Program, University of Florida, FL, 32611
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  • For correspondence: jkim6@ufl.edu
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Abstract

Aldoximes are amino acid derivatives that serve as intermediates for numerous specialized metabolites including cyanogenic glycosides, glucosinolates, and auxins. Aldoxime formation is mainly catalyzed by cytochrome P450 monooxygenases of the 79 family (CYP79s) that can have broad or narrow substrate specificity. Aldoxime biosynthesis in the cereal sorghum (Sorghum bicolor) is not well characterized. This study identified nine CYP79-encoding genes in the genome of sorghum. A phylogenetic analysis of CYP79 showed that SbCYP79A61 formed a subclade with maize ZmCYP79A61, previously characterized to be involved in aldoxime biosynthesis. Functional characterization of this sorghum enzyme using transient expression in Nicotiana benthamiana and stable overexpression in Arabidopsis thaliana revealed that SbCYP79A61 catalyzes the production of phenylacetaldoxime (PAOx) from phenylalanine, but unlike the maize enzyme, displays no detectable activity against tryptophan. Additionally, targeted metabolite analysis after stable isotope feeding assays revealed that PAOx can serve as a precursor of phenylacetic acid (PAA) in sorghum and identified benzyl cyanide as an intermediate of PAOx-derived PAA biosynthesis in both sorghum and maize. Taken together, our results demonstrate that SbCYP79A61 produces PAOx in sorghum and may serve in the biosynthesis of other nitrogen-containing phenylalanine-derived metabolites involved in mediating biotic and abiotic stresses.

Competing Interest Statement

The authors have declared no competing interest.

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Posted May 11, 2022.
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SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor
Veronica C. Perez, Ru Dai, Breanna Tomiczek, Jorrel Mendoza, Emily S.A. Wolf, Alexander Grenning, Wilfred Vermerris, Anna K. Block, Jeongim Kim
bioRxiv 2022.05.11.491506; doi: https://doi.org/10.1101/2022.05.11.491506
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SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor
Veronica C. Perez, Ru Dai, Breanna Tomiczek, Jorrel Mendoza, Emily S.A. Wolf, Alexander Grenning, Wilfred Vermerris, Anna K. Block, Jeongim Kim
bioRxiv 2022.05.11.491506; doi: https://doi.org/10.1101/2022.05.11.491506

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