Engineering of new-to-nature halogenated indigo precursors in plants

Metabolic Engineering - Tập 46 - Trang 20-27 - 2018
Sabine Fräbel1, Bastian Wagner1, Markus Krischke2, Volker Schmidts3, Christina M. Thiele3, Agata Staniek1, Heribert Warzecha1
1Plant Biotechnology and Metabolic Engineering, Technische Universität Darmstadt, Schnittspahnstraße 4, 64287 Darmstadt, Germany
2Lehrstuhl für Pharmazeutische Biologie, Julius-von-Sachs-Institut der Universität Würzburg, Julius-von-Sachs-Platz 2, 97082 Würzburg, Germany
3Clemens-Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Alarich-Weiss-Str. 4, 64287 Darmstadt, Germany

Tài liệu tham khảo

Barbier-Brygoo, 2000, Anion channels in higher plants: functional characterization, molecular structure, and physiological role, Biochim. Biophys. Acta, 1465, 199, 10.1016/S0005-2736(00)00139-5 Benkendorff, 2013, Natural product research in the Australian marine invertebrate Dicathais orbita, Mar. Drugs, 11, 1370, 10.3390/md11041370 Bernhardt, 2007, Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle, Chem. Biol., 14, 888, 10.1016/j.chembiol.2007.07.008 Böttcher, 2015, Synthesis of indoxyl-glycosides for detection of glycosidase activities, J. Vis. Exp., e52442 Brown, 2015, De novo production of the plant-derived alkaloid strictosidine in yeast, Proc. Natl. Acad. Sci. USA, 112, 3205, 10.1073/pnas.1423555112 Deb Roy, 2010, Gene expression enabling synthetic diversification of natural products: chemogenetic generation of pacidamycin analogs, J. Am. Chem. Soc., 132, 12243, 10.1021/ja1060406 Dong, 2005, Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination, Science, 309, 2216, 10.1126/science.1116510 Findeisen, 2007, A 1H-NMR thermometer suitable for cryoprobes, Magn. Reson. Chem., 45, 175, 10.1002/mrc.1941 Fischbach, 2007, One pathway, many products, Nat. Chem. Biol., 3, 353, 10.1038/nchembio0707-353 Foroozandeh, 2016, Ultrahigh-resolution diffusion-ordered spectroscopy, Angew. Chem. Int. Ed. Engl., 55, 15579, 10.1002/anie.201609676 Fräbel, 2016, Recombinant flavin-dependent halogenases are functional in tobacco chloroplasts without co-expression of flavin reductase genes, Biotechnol. J., 11, 1586, 10.1002/biot.201600337 Gilbert, 2001, Dyes from plants: past usage, present understanding, and potential, Plant Growth Regul., 34, 57, 10.1023/A:1013374618870 Hawkins, 2008, Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae, Nat. Chem. Biol., 4, 564, 10.1038/nchembio.105 Kiernan, 2007, Indigogenic substrates for detection and localization of enzymes, Biotech. Histochem., 82, 73, 10.1080/10520290701375278 Kling, 2005, Enzymatic incorporation of halogen atoms into natural compounds, Ernst Scher. Res. Found. Workshop, 51, 165, 10.1007/3-540-27055-8_8 Koos, 2016, CLIP-COSY: a clean in-phase experiment for the rapid acquisition of COSY-type correlations, Angew. Chem. Int. Ed. Engl., 55, 7655, 10.1002/anie.201510938 Lassen, 2014, Redirecting photosynthetic electron flow into light-driven synthesis of alternative products including high-value bioactive natural compounds, ACS Synth. Biol., 3, 1, 10.1021/sb400136f Lee, 1995, The mechanism of Escherichia coli tryptophan indole-lyase: substituent effects on steady-state and pre-steady-state kinetic parameters for aryl-substituted tryptophan derivatives, Bioorg. Med. Chem., 3, 195, 10.1016/0968-0896(95)00016-A Loris, 2007, Structure-based engineering of strictosidine synthase: auxiliary for alkaloid libraries, Chem. Biol., 14, 979, 10.1016/j.chembiol.2007.08.009 Nakamura, 2001, Random mutagenesis of human cytochrome P450 2A6 and screening with indole oxidation products, Arch. Biochem. Biophys., 395, 25, 10.1006/abbi.2001.2569 O'Keefe, 1994, Plant expression of a bacterial cytochrome P450 that catalyzes activation of a sulfonylurea pro-herbicide, Plant Physiol., 105, 473, 10.1104/pp.105.2.473 Patron, 2015, Standards for plant synthetic biology: a common syntax for exchange of DNA parts, New Phytol., 208, 13, 10.1111/nph.13532 Payne, 2013, Regioselective arene halogenation using the FAD-dependent halogenase RebH, Angew. Chem. Int. Ed. Engl., 52, 5271, 10.1002/anie.201300762 Reed, 2017, A translational synthetic biology platform for rapid access to gram-scale quantities of novel drug-like molecules, Metab. Eng., 42, 185, 10.1016/j.ymben.2017.06.012 Ro, 2006, Production of the antimalarial drug precursor artemisinic acid in engineered yeast, Nature, 440, 940, 10.1038/nature04640 Runguphan, 2010, Integrating carbon-halogen bond formation into medicinal plant metabolism, Nature, 468, 461, 10.1038/nature09524 Sanchez, 2005, Combinatorial biosynthesis of antitumor indolocarbazole compounds, Proc. Natl. Acad. Sci. USA, 102, 461, 10.1073/pnas.0407809102 Sarrion-Perdigones, 2013, GoldenBraid 2.0: a comprehensive DNA assembly framework for plant synthetic biology, Plant Physiol., 162, 1618, 10.1104/pp.113.217661 Staniek, 2013, Natural products – modifying metabolite pathways in plants, Biotechnol. J., 8, 1159, 10.1002/biot.201300224 Staniek, 2014, Natural products – learning chemistry from plants, Biotechnol. J., 9, 326, 10.1002/biot.201300059 Thrippleton, 2003, Elimination of zero-quantum interference in two-dimensional NMR spectra, Angew. Chem. Int. Ed. Engl., 42, 3938, 10.1002/anie.200351947 van Pee, 2006, Flavin-dependent halogenases involved in secondary metabolism in bacteria, Appl. Microbiol. Biotechnol., 70, 631, 10.1007/s00253-005-0232-2 Warzecha, 2007, Formation of the indigo precursor indican in genetically engineered tobacco plants and cell cultures, Plant Biotechnol. J., 5, 185, 10.1111/j.1467-7652.2006.00231.x