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

Metabolic Engineering
Sabine FräbelHeribert Warzecha

Abstract

Plants are versatile chemists producing a tremendous variety of specialized compounds. Here, we describe the engineering of entirely novel metabolic pathways in planta enabling generation of halogenated indigo precursors as non-natural plant products. Indican (indolyl-β-D-glucopyranoside) is a secondary metabolite characteristic of a number of dyers plants. Its deglucosylation and subsequent oxidative dimerization leads to the blue dye, indigo. Halogenated indican derivatives are commonly used as detection reagents in histochemical and molecular biology applications; their production, however, relies largely on chemical synthesis. To attain the de novo biosynthesis in a plant-based system devoid of indican, we employed a sequence of enzymes from diverse sources, including three microbial tryptophan halogenases substituting the amino acid at either C5, C6, or C7 of the indole moiety. Subsequent processing of the halotryptophan by bacterial tryptophanase TnaA in concert with a mutant of the human cytochrome P450 monooxygenase 2A6 and glycosylation of the resulting indoxyl derivatives by an endogenous tobacco glucosyltransferase yielded corresponding haloindican variants in transiently transformed Nicotiana benthamiana plants. Acc...Continue Reading

Citations

Dec 14, 2019·Applied Microbiology and Biotechnology·Andrea N Fabara, Marco W Fraaije
Mar 10, 2020·Current Protocols in Molecular Biology·Marta Vazquez-VilarDiego Orzaez
Apr 23, 2020·Biotechnology for Biofuels·Chien-Yuan Lin, Aymerick Eudes
Nov 17, 2020·Frontiers in Bioengineering and Biotechnology·Samuel A BradleyMichael K Jensen
Jan 27, 2021·Chemistry : a European Journal·Christian SchnepelNorbert Sewald

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