Horseradish peroxidase-catalyzed oligomerization of ferulic acid on a template of a tyrosine-containing tripeptide.
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.
Oudgenoeg
Gideon
G
Centre for Protein Technology TNO-WU, Bomenweg 2, 6700 EV Wageningen, The Netherlands.
Dirksen
Eef
E
Ingemann
Steen
S
Hilhorst
Riet
R
Gruppen
Harry
H
Boeriu
Carmen G
CG
Piersma
Sander R
SR
van Berkel
Willem J H
WJ
Laane
Colja
C
Voragen
Alphons G J
AG
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
D003373:Coumaric Acids; D010455:Peptides; D014443:Tyrosine; C004999:ferulic acid; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase; D010100:Oxygen; D005998:Glycine