Abstract
Cell-free extracts from leaves of Rhus typhina L. (sumach) were found to transfer the 1-O-galloyl moiety of l,6-di-O-galloyl-β-d-glucose to the 2-position of the same compound, yielding 1,2,6-tri-O-galloyl-β-d-glucose and leaving 6-O-galloylglucose as the deacylated by-product. The enzyme catalyzing this ‘disproportionation’ was purified almost 1700-fold. It had a molecular weight of approx. 56 000, a K m value of 11.5 mM, was stable between pH 4.5 and 6.5, and most active at pH 5.9 and 40° C. The systematic name “1,6-di-O-galloyl-glucose: 1,6-di-O-galloylglucose 2-O-galloyltransferase” (EC 2.3.1.) was proposed for this new enzyme whose detection provided evidence that, in addition to β-glucogallin (1-O-galloyl-β-d-glucose), higher substituted glucose esters also have the potential to serve as acyl donors in the biosynthesis of gallotannins.
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Abbreviations
- HPLC:
-
high-performance liquid chromatography
- RP:
-
reversed-phase
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We thank Mrs. U. Denzel for skillfull technical assistance, and Professors E. Haslam (Department of Chemistry, University of Sheffield, UK) and G. Nonaka (Kyshu University, Fukuoka, Japan) for providing reference substances. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.
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Denzel, K., Gross, G.G. Biosynthesis of gallotannins. Planta 184, 285–289 (1991). https://doi.org/10.1007/BF00197959
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DOI: https://doi.org/10.1007/BF00197959