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Tailoring Natural Products with Glycosyltransferases

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Biotechnology of Natural Products

Abstract

The bioactivity of plant natural products depends on more than just their scaffolds. The physicochemical properties of the natural products are often dramatically changed by tailoring functional groups. Addition of sugar residues (glycons) to small lipophilic molecules (aglycons) is a particularly frequent tailoring mechanism mostly conveyed by nucleoside diphosphate (NDP)-sugar dependent glycosyltransferases (GTs). Glycosylation increases solubility and stability, while also reducing the toxicity of the aglycons. Moreover, the attachment of a sugar may determine the fate of the molecule by controlling its compartmentalization. Above all, glycosylation affects bioactivity and bioavailability. Consequently, glycosides and glucose esters of bioactive natural products have become of utmost importance for the food, feed, cosmetics and pharmaceutical industry. In the past, glycosylation was achieved chemically involving flammable solvents and toxic catalysts, harsh laboratory conditions and the necessity of protecting groups, which eventually resulted in high costs. Nowadays, alternative biotechnological methods are available. Cultivation of whole-cell biocatalysts harboring GTs enables the regio- and stereo-selective production of glycosides and glucose esters at high product titers, while keeping the costs at a minimum. Due to their sedentary life style, plants have to cope with numerous stressors and, because glycosylated natural products play important roles in stress defense, are also rich sources of GTs. This chapter covers the last 10 years of plant GT research, with special emphasis upon new enzymes and glycoside/glucose ester production of plant natural products by whole-cell biocatalysts.

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Abbreviations

ABA:

Abscisic acid

ABA-GE:

ABA-glucose ester

ABC:

ATP-binding cassette

AG:

Apocarotenoid glycoside

AVI:

Anthocyanin vacuolar inclusion

CAZymes:

Carbohydrate-Active enZymes

CRC:

Colorectal cancer

E. coli :

Escherichia coli

ER:

Endoplasmatic reticulum

GALNT12:

Polypeptide N-acetylgalactosaminyltransferase 12

galU:

Glucose-1-phosphate uridylyltransferase

GST:

Glutathione S-transferase

GT:

Glycosyltransferase

KAH:

Kaurenoic acid 13-hydroxylase

KO:

Kaurine oxidase

LC-MS:

Liquid chromatography mass-spectrometry

MATE:

Multidrug and toxic extrusion

MEP/DOXP:

2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate

MXT:

Mitoxantrole

pgi:

Phosphoglucose isomerase

PSPG box:

Plant secondary product glycosyltransferase box

SG:

Steviol glycoside

ushA:

UDP-glucose hydrolase

zwf:

D-glucose-6-phosphate dehydrogenase

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  1. Biotechnology of Natural Products, Technische Universität München, Liesel-Beckmann-Str. 1, 85354, Freising, Germany

    Katja Härtl, Kate McGraphery, Julian Rüdiger & Wilfried Schwab

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    Wilfried Schwab

  2. Institute of Biological Chemistry and M.J. Murdock Metabolomics Laboratory, Washington State University, Pullman, Washington, USA

    Bernd Markus Lange

  3. Bioanalytics, Institute of Nutritional and Food Sciences (IEL), University of Bonn, Bonn, Germany

    Matthias Wüst

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Härtl, K., McGraphery, K., Rüdiger, J., Schwab, W. (2018). Tailoring Natural Products with Glycosyltransferases. In: Schwab, W., Lange, B., Wüst, M. (eds) Biotechnology of Natural Products. Springer, Cham. https://doi.org/10.1007/978-3-319-67903-7_9

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