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Volume 18, Issue 3, Pages 354-360 (March 2011) Ralfuranone Biosynthesis in Ralstonia solanacearum Suggests Functional Divergence in the Quinone Synthetase Family of Enzymes Barbara Wackler, Patrick Schneider, Jonathan M. Jacobs, Julia Pauly, Caitilyn Allen, Markus Nett, Dirk Hoffmeister Chemistry & Biology Volume 18, Issue 3, Pages 354-360 (March 2011) DOI: 10.1016/j.chembiol.2011.01.010 Copyright © 2011 Elsevier Ltd Terms and Conditions

Figure 1 Chemical Structures of Ralstonia Metabolites Ralfuranone (1) and Ralfuranone B (2), and Related Natural Products of Other Sources Chemistry & Biology 2011 18, 354-360DOI: (10.1016/j.chembiol.2011.01.010) Copyright © 2011 Elsevier Ltd Terms and Conditions

Figure 2 Physical Map of Ralfuranone Biosynthesis Genes ralA and ralD and Adjacent Reading Frames Open arrows represent hypothetical genes; gray arrows represent putative natural product biosynthesis and transporter genes (details in Table S1). The layout of multidomain enzymes is shown below their genes. A, adenylation domain; C, condensation domain; T, thiolation domain; TE, thioesterase domain. For clarity, the domain order within the enzymes is shown in opposite direction to the transcriptional orientation of the gene. Chemistry & Biology 2011 18, 354-360DOI: (10.1016/j.chembiol.2011.01.010) Copyright © 2011 Elsevier Ltd Terms and Conditions

Figure 3 HPLC Chromatograms of R. solanacearum Crude Extracts Wild-type strain GMI 1000 (WT), and the ralA, RSp1422, and ralD knockout strains (RSp1419::Kmr, RSp1422::Kmr, and RSp1424::Kmr). The signals at 19.2 and 21.3 min represent ralfuranone and ralfuranone B, respectively. The peak at 22.0 min corresponds to a hydroxylated ralfuranone derivative (m/z 176) described in (Schneider et al., 2009). Chemistry & Biology 2011 18, 354-360DOI: (10.1016/j.chembiol.2011.01.010) Copyright © 2011 Elsevier Ltd Terms and Conditions

Figure 4 Potential RalA A-Domain Substrates Tested with the ATP-Pyrophosphate Exchange Assay Relative activities are referenced to phenylpyruvic acid turnover. Upper row (left to right): phenylpyruvic acid, 4-hydroxyphenylpyruvic acid, L-phenylalanine, and cinnamic acid, lower row (left to right) phenylglyoxylic acid, mandelic acid, phenylglycine, and phenylacetic acid. Chemistry & Biology 2011 18, 354-360DOI: (10.1016/j.chembiol.2011.01.010) Copyright © 2011 Elsevier Ltd Terms and Conditions

Figure 5 Proposed Route of Furanone Biosynthesis in R. solanacearum, Involving Aminotransferase and Furanone Synthetase Activity IP, imidazol-5-yl-pyruvate; HPP, 4-hydroxyphenylpyruvate; Pyr, pyruvate. For stable isotope feeding experiment data, see Figure S1. Chemistry & Biology 2011 18, 354-360DOI: (10.1016/j.chembiol.2011.01.010) Copyright © 2011 Elsevier Ltd Terms and Conditions