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Predicting the substrate specificity of a glycosyltransferase implicated in the production of phenolic volatiles in tomato fruit

Louveau, Thomas and Leitao, Céline and Green, Sol and Hamiaux, Cyril and Van der Rest, Benoît and Dechy-Cabaret, Odile and Atkinson, Ross G. and Chervin, Christian Predicting the substrate specificity of a glycosyltransferase implicated in the production of phenolic volatiles in tomato fruit. (2011) FEBS Journal, vol. 278 (n°2). pp. 390-400. ISSN 1742-4658

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Official URL: http://dx.doi.org/10.1111/j.1742-4658.2010.07962.x

Abstract

The volatile compounds that constitute the fruit aroma of ripe tomato (Solanum lycopersicum) are often sequestered in glycosylated form. A homology-based screen was used to identify the gene SlUGT5, which is a member of UDP-glycosyltransferase 72 family and shows specificity towards a range of substrates, including flavonoid, flavanols, hydroquinone, xenobiotics and chlorinated pollutants. SlUGT5 was shown to be expressed primarily in ripening fruit and flowers, and mapped to chromosome I in a region containing a QTL that affected the content of guaiacol and eugenol in tomato crosses. Recombinant SlUGT5 protein demonstrated significant activity towards guaiacol and eugenol, as well as benzyl alcohol and methyl salicylate; however, the highest in vitro activity and affinity was shown for hydroquinone and salicyl alcohol. NMR analysis identified isosalicin as the only product of salicyl alcohol glycosylation. Protein modelling and substrate docking analysis were used to assess the basis for the substrate specificity of SlUGT5. The analysis correctly predicted the interactions with SlUGT5 substrates, and also indicated that increased hydrogen bonding, due to the presence of a second hydrophilic group in methyl salicylate, guaiacol and hydroquinone, appeared to more favourably anchor these acceptors within the glycosylation site, leading to increased stability, higher activities and higher substrate affinities.

Item Type:Article
Additional Information:Thanks to Wiley Blackwell publisher. The definitive version is available at http://onlinelibrary.wiley.com/doi/10.1111/j.1742-4658.2010.07962.x/abstract
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS
Université de Toulouse > Institut National Polytechnique de Toulouse - INPT
French research institutions > Institut National de la Recherche Agronomique - INRA
Other partners > John Innes Centre (UNITED KINGDOM)
Other partners > The New Zealand Institute for Plant & Food Research (NEW ZEALAND)
Other partners > Université de Strasbourg - UNISTRA (FRANCE)
Université de Toulouse > Université Paul Sabatier-Toulouse III - UPS
Laboratory name:
Statistics:download
Deposited By: Brigitte LAFFORGUE

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