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. 2020 Jan 22;6(2):197–206. doi: 10.1021/acscentsci.9b01076

Figure 3.

Figure 3

Formation of dipeptide ketone intermediates. (A) Proposed DPO (7) pathway. (B) Pyrazinones 1, 2, 4, and 5 would be generated from their corresponding dipeptide ketone precursors. (C) Proposed pathway of 6 from two molecules of AA. See Figure 4D for full pathway. (D) Time-course analysis for production of metabolites 1, 2, 4, and 5, and their linear precursors in E. coli Nissle 1917. n = 3 biological replicates. Data are mean ± SD. (E) Biomimetic synthesis of 1, 2, 4, and 5. Linear-1, -2, -4, and -5 spontaneously converted to 1, 2, 4, and 5, respectively. (F) Selective in vitro synthesis of linear-1, -2, -4, and -5 using PURExpress in vitro protein synthesis technologies. (G) Aminoketone (AMB/AA) dose-dependent production of linear-1 and -2 was observed. The Extracted Ion Chromatograms (EICs) were generated with a 10 ppm error window. (H) Presence of tRNAs decreased production of linear-1 and -2. n = 2 (linear-1) or 3 (linear-2) biological replicates. Data are mean ± SD; *P < 0.05, **P < 0.01. Two-tailed t-test.