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Horseradish peroxidase-catalyzed oligomerization of ferulic acid on a template of a tyrosine-containing tripeptide

Author: Oudgenoeg, G. · Dirksen, E. · Ingemann, S. · Hilhorst, R. · Gruppen, H. · Boeriu, C.G. · Piersma, S.R. · Berkel, W.J.H. van · Laane, C. · Voragen, A.G.J.
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Journal of Biological Chemistry, 24, 277, 21332-21340
Identifier: 87773
doi: doi:10.1074/jbc.M201679200
Keywords: Biology · Cell Wall · Chromatography, High Pressure Liquid · Coumaric Acids · Glycine · Horseradish Peroxidase · Hydrogen Peroxide · Kinetics · Mass Spectrometry · Models, Chemical · Oxygen · Peptides · Plants · Spectrometry, Mass, Electrospray Ionization · Time Factors · Tyrosine · Armoracia rusticana


Ferulic acid (FA) is an abundantly present phenolic constituent of plant cell walls. Kinetically controlled incubation of FA and the tripeptide Gly-Tyr-Gly (GYG) with horseradish peroxidase and H2O2 yielded a range of new cross-linked products. Two predominant series of hetero-oligomers of FA linked by dehydrogenation to the peptidyl tyrosine were characterized by electrospray ionization (tandem) mass spectrometry. One series comprises GYG coupled with 4-7 FA moieties linked by dehydrogenation, of which one is decarboxylated. In the second series 4-9 FA moieties linked by dehydrogenation, of which two are decarboxylated, are coupled to the tripeptide. A third series comprises three heterooligomers in which the peptidyl tyrosine is linked to 1-3 FA moieties of which none is decarboxylated. Two mechanisms for the formation of the FA-Tyr oligomers that result from the dualistic, concentration-dependent chemistry of FA and their possible role in the regulation of plant cell wall tissue growth are presented. Chemicals/CAS: Coumaric Acids; ferulic acid, 1135-24-6; Glycine, 56-40-6; Horseradish Peroxidase, EC 1.11.1.-; Hydrogen Peroxide, 7722-84-1; Oxygen, 7782-44-7; Peptides; Tyrosine, 55520-40-6