title: Horseradish peroxidase-catalyzed oligomerization of ferulic acid on a template of a tyrosine-containing tripeptide.
abstract: 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 hetero-oligomers 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.
authors.affiliation: Centre for Protein Technology TNO-WU, Bomenweg 2, 6700 EV Wageningen, The Netherlands.
authors.forename: Gideon
authors.initials: G
authors.lastname: Oudgenoeg
authors.forename: Eef
authors.initials: E
authors.lastname: Dirksen
authors.forename: Steen
authors.initials: S
authors.lastname: Ingemann
authors.forename: Riet
authors.initials: R
authors.lastname: Hilhorst
authors.forename: Harry
authors.initials: H
authors.lastname: Gruppen
authors.forename: Carmen G
authors.initials: CG
authors.lastname: Boeriu
authors.forename: Sander R
authors.initials: SR
authors.lastname: Piersma
authors.forename: Willem J H
authors.initials: WJ
authors.lastname: van Berkel
authors.forename: Colja
authors.initials: C
authors.lastname: Laane
authors.forename: Alphons G J
authors.initials: AG
authors.lastname: Voragen
mesh_terms: D002473:Cell Wall / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000737:chemistry* / Q000378:metabolism*; D005998:Glycine / Q000737:chemistry; D006735:Horseradish Peroxidase / Q000494:pharmacology*; D006861:Hydrogen Peroxide / Q000494:pharmacology; D007700:Kinetics; D013058:Mass Spectrometry; D008956:Models, Chemical; D010100:Oxygen / Q000378:metabolism; D010455:Peptides / Q000737:chemistry*; D010944:Plants / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013997:Time Factors; D014443:Tyrosine / Q000737:chemistry* / Q000378:metabolism
chemical_list: D003373:Coumaric Acids; D010455:Peptides; D014443:Tyrosine; C004999:ferulic acid; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase; D010100:Oxygen; D005998:Glycine