Synthesis of Unnatural Flavonoids and Stilbenes by Exploiting the Plant Biosynthetic Pathway in Escherichia coli Yohei Katsuyama, Nobutaka Funa, Ikuo.

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Presentation transcript:

Synthesis of Unnatural Flavonoids and Stilbenes by Exploiting the Plant Biosynthetic Pathway in Escherichia coli Yohei Katsuyama, Nobutaka Funa, Ikuo Miyahisa, Sueharu Horinouchi Chemistry & Biology Volume 14, Issue 6, Pages 613-621 (June 2007) DOI: 10.1016/j.chembiol.2007.05.004 Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 1 Synthesis Routes of Plant Polyketides in Plants and Recombinant E. coli (A) Biosynthesis of flavanones and stilbenes in plants. These key intermediates are further modified into flavones and flavonols. (B) The multiplasmid approach for synthesis of unnatural plant polyketides in E. coli. The polyketide synthesis is divided into three steps: substrate synthesis from carboxylic acids by LE4CL-1, polyketide biosynthesis by CHS/CHI and STS, and modification by FNS and F3H/FLS. Chemistry & Biology 2007 14, 613-621DOI: (10.1016/j.chembiol.2007.05.004) Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 2 Summary of the Structures of Plant Polyketides Produced in This Study The polyketides synthesized are surrounded by red squares. Novel compounds, which have not been reported in the literature, are indicated in blue. Chemistry & Biology 2007 14, 613-621DOI: (10.1016/j.chembiol.2007.05.004) Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 3 Extracted Ion LC-ESI/MS Chromatograms and LC-ESI/MS/MS Fragmentation Spectra of 8g and 8f (A) E. coli harboring pCDF-LE4CL-1, pRSF-ACC, pETDuet-1, and pACYCDuet-1, as a negative control, produced no flavanones. The target ions of the extracted ion chromatograms are shown in the upper right of the chromatograms. (B) Supplementation of 8a to E. coli harboring pCDF-LE4CL-1, pRSF-ACC, pET-CHS/CHI, and pACYCDuet-1 led to production of 8g. (C) E. coli harboring pCDF-LE4CL-1, pRSF-ACC, pETDuet-1, and pACYCDuet-1, as a negative control, produced no stilbenes. The target ions of the extracted ion chromatograms are shown in the upper right of the chromatograms. (D) Supplementation of 8a to E. coli harboring pCDF-LE4CL-1, pRSF-ACC, pET-STS, and pACYCDuet-1 led to production of 8f. (E) The LC-ESI/MS/MS fragmentation spectrum of 8g. (F) The LC-ESI/MS/MS fragmentation spectrum of 8f. Chemistry & Biology 2007 14, 613-621DOI: (10.1016/j.chembiol.2007.05.004) Copyright © 2007 Elsevier Ltd Terms and Conditions