Structure-function relationship of terpenoid glycosyltransferases from plants

Covering: up to 2021 Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scie...

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Published inNatural product reports Vol. 39; no. 2; pp. 389 - 49
Main Authors Kurze, Elisabeth, Wüst, Matthias, Liao, Jieren, McGraphery, Kate, Hoffmann, Thomas, Song, Chuankui, Schwab, Wilfried
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 23.02.2022
Subjects
Crystal structure
diterpenoids
Enantiomers
enantioselectivity
Glycosylation
Glycosyltransferase
glycosyltransferases
Physicochemical properties
Polarity
solubility
structure-activity relationships
Structure-function relationships
Substrates
Terpenes
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Abstract Covering: up to 2021 Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scientific progress has been made in the functional study of glycosylated terpenes and numerous plant enzymes involved in regio- and enantioselective glycosylation have been characterized, a reaction that remains chemically challenging. Crucial clues to the mechanism of terpenoid glycosylation were recently provided by the first crystal structures of a diterpene glycosyltransferase UGT76G1. Here, we review biochemically characterized terpenoid glycosyltransferases, compare their functions and primary structures, discuss their acceptor and donor substrate tolerance and product specificity, and elaborate features of the 3D structures of the first terpenoid glycosyltransferases from plants. The spatial size of the catalytic centre and a large hydrophobic pocket in the active site affect the enzymatic activity and substrate preference of uridine diphosphate-sugar-dependent terpenoid glycosyltransferases in plants.
AbstractList Covering: up to 2021Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scientific progress has been made in the functional study of glycosylated terpenes and numerous plant enzymes involved in regio- and enantioselective glycosylation have been characterized, a reaction that remains chemically challenging. Crucial clues to the mechanism of terpenoid glycosylation were recently provided by the first crystal structures of a diterpene glycosyltransferase UGT76G1. Here, we review biochemically characterized terpenoid glycosyltransferases, compare their functions and primary structures, discuss their acceptor and donor substrate tolerance and product specificity, and elaborate features of the 3D structures of the first terpenoid glycosyltransferases from plants.
Covering: up to 2021 Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scientific progress has been made in the functional study of glycosylated terpenes and numerous plant enzymes involved in regio- and enantioselective glycosylation have been characterized, a reaction that remains chemically challenging. Crucial clues to the mechanism of terpenoid glycosylation were recently provided by the first crystal structures of a diterpene glycosyltransferase UGT76G1. Here, we review biochemically characterized terpenoid glycosyltransferases, compare their functions and primary structures, discuss their acceptor and donor substrate tolerance and product specificity, and elaborate features of the 3D structures of the first terpenoid glycosyltransferases from plants. The spatial size of the catalytic centre and a large hydrophobic pocket in the active site affect the enzymatic activity and substrate preference of uridine diphosphate-sugar-dependent terpenoid glycosyltransferases in plants.
Covering: up to 2021
Covering: up to 2021Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scientific progress has been made in the functional study of glycosylated terpenes and numerous plant enzymes involved in regio- and enantioselective glycosylation have been characterized, a reaction that remains chemically challenging. Crucial clues to the mechanism of terpenoid glycosylation were recently provided by the first crystal structures of a diterpene glycosyltransferase UGT76G1. Here, we review biochemically characterized terpenoid glycosyltransferases, compare their functions and primary structures, discuss their acceptor and donor substrate tolerance and product specificity, and elaborate features of the 3D structures of the first terpenoid glycosyltransferases from plants.Covering: up to 2021Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scientific progress has been made in the functional study of glycosylated terpenes and numerous plant enzymes involved in regio- and enantioselective glycosylation have been characterized, a reaction that remains chemically challenging. Crucial clues to the mechanism of terpenoid glycosylation were recently provided by the first crystal structures of a diterpene glycosyltransferase UGT76G1. Here, we review biochemically characterized terpenoid glycosyltransferases, compare their functions and primary structures, discuss their acceptor and donor substrate tolerance and product specificity, and elaborate features of the 3D structures of the first terpenoid glycosyltransferases from plants.
Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in terms of polarity, volatility, solubility and reactivity, and their bioactivities are altered accordingly. Significant scientific progress has been made in the functional study of glycosylated terpenes and numerous plant enzymes involved in regio- and enantioselective glycosylation have been characterized, a reaction that remains chemically challenging. Crucial clues to the mechanism of terpenoid glycosylation were recently provided by the first crystal structures of a diterpene glycosyltransferase UGT76G1. Here, we review biochemically characterized terpenoid glycosyltransferases, compare their functions and primary structures, discuss their acceptor and donor substrate tolerance and product specificity, and elaborate features of the 3D structures of the first terpenoid glycosyltransferases from plants.
Author Wüst, Matthias
McGraphery, Kate
Schwab, Wilfried
Liao, Jieren
Kurze, Elisabeth
Song, Chuankui
Hoffmann, Thomas
AuthorAffiliation Technische Universität München
TUM School of Life Sciences
University of Bonn
State Key Laboratory of Tea Plant Biology and Utilization
Institute of Nutritional and Food Sciences
International Joint Laboratory on Tea Chemistry and Health Effects
Chair of Food Chemistry
Biotechnology of Natural Products
Anhui Agricultural University Hefei
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– name: State Key Laboratory of Tea Plant Biology and Utilization
– name: TUM School of Life Sciences
– name: Anhui Agricultural University Hefei
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Dedicated to Professor Rodney Croteau in honour of his 75th birthday.
Electronic supplementary information (ESI) available. See DOI
Elisabeth Kurze received her MSc in Biochemistry from the University of Leipzig and completed her PhD at TUM in 2019. Matthias Wüst received his PhD in Food Chemistry from the University of Frankfurt/Main. He has been Full Professor of Food Chemistry at the University of Bonn since 2009. Liao Jieren obtained her MSc in tea bioengineering at Nanjing Agriculture University in 2019. She is currently carrying out PhD research at TUM. Kate McGraphery completed her master's degree in Molecular Biology LMU and her bachelor's degree in Biochemistry in Toronto. She received her PhD from TUM in 2020. Thomas Hoffmann studied Food Chemistry at LMU and received his PhD in 2001 from TUM. Since 2004, he has been working at the professorship Biotechnology of Natural Products TUM. Chuankui Song obtained his PhD (2015) at TUM. He established his own research group at the State Key Laboratory of Tea Plant Biology and Utilization of Anhui Agricultural University in 2016. Wilfried Schwab received his PhD in Food Chemistry from the University of Würzburg in 1989. He joined Hoechst AG in 1991. In 2003, he was awarded an Endowed Chair at TUM and has been Professor of Biotechnology of Natural Products since 2010.
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Snippet Covering: up to 2021 Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by...
Covering: up to 2021
Covering: up to 2021Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by...
Terpenoids are physiologically active substances that are of great importance to humans. Their physicochemical properties are modified by glycosylation, in...
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SubjectTerms Crystal structure
diterpenoids
Enantiomers
enantioselectivity
Glycosylation
Glycosyltransferase
glycosyltransferases
Physicochemical properties
Polarity
solubility
structure-activity relationships
Structure-function relationships
Substrates
Terpenes
Title Structure-function relationship of terpenoid glycosyltransferases from plants
URI https://www.ncbi.nlm.nih.gov/pubmed/34486004
https://www.proquest.com/docview/2631960278
https://www.proquest.com/docview/2569617189
https://www.proquest.com/docview/2661042585
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