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ARS Home » Pacific West Area » Corvallis, Oregon » Forage Seed and Cereal Research Unit » Research » Publications at this Location » Publication #395567
Research Project: Improving Plant, Soil, and Cropping Systems Health and Productivity through Advanced Integration of Comprehensive Management Practices

Location: Forage Seed and Cereal Research Unit

Title: Biosynthetic origin of formylaminooxyvinylglycine and characterization of the formyltransferase GvgI

Author
item LESCALLETTE, ADAM - University Of North Carolina
item DUNN, ZACHARY - University Of North Carolina
item Manning, Viola
item Trippe, Kristin
item LI, BO - University Of North Carolina

Submitted to: Biochemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/12/2022
Publication Date: 9/20/2022
Citation: Lescallette, A.R., Dunn, Z.D., Manning, V., Trippe, K.M., Li, B. 2022. Biosynthetic origin of formylaminooxyvinylglycine and characterization of the formyltransferase GvgI. Biochemistry. 61(19):2159-2164. https://doi.org/10.1021/acs.biochem.2c00374.
DOI: https://doi.org/10.1021/acs.biochem.2c00374

Interpretive Summary: 4-Formylaminooxyvinylglycine (FVG) is a naturally-occurring herbicide produced by soil bacteria. FVG is an attractive target for commercial development because it specifically targets the germination of grasses and can be used to control weeds in perennial grasses and broadleaf crops. However, commercial deployment of FVG is limited because the compound cannot be artificially synthesized. Therefore, large scale FVG production can only be accomplished through biological pathways. To develop that technology, we must first understand the pathways that are used by bacteria to synthesize FVG. This study used various bacterial strains to isolate and identify steps and intermediates in the biosynthetic pathway. Likewise, this study characterized the enzymes used to mediate those steps. The results of this study confirm previous hypotheses regarding steps in the FVG pathway and lends insight into strategies that may be used to develop FVG-based herbicides.

Technical Abstract: 4-Formylaminooxyvinylglycine (FVG) is an herbicidal and antibacterial nonproteinogenic amino acid produced by several strains of the Pseudomonas fluorescens species complex. It contains a unique vinyl alkoxyamine moiety with an O-N bond and its biosynthetic origin remains unknown. Here, we show that the gvg cluster from P. fluorescens WH6 is responsible for biosynthesis of FVG and two additional O-N bond-containing oxyvinylglycines, guanidinooxyvinylglycine and aminooxyvinylglycine. Bacterial feeding studies indicate that these compounds originate from homoserine. We identify a formyltransferase gvgI that is required for the production of FVG and characterize the activity of this enzyme in vitro toward amino acids with a side chain amine. Sequence similarity network analysis suggests that G vgI represents a class of natural product formyltransferases that catalyze N-formylations of amino acid substrates.