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

The Journal of Biological Chemistry
G OudgenoegA G Voragen

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.

References

Mar 31, 1995·The Journal of Biological Chemistry·M A BernardsN G Lewis
Oct 12, 2000·Carbohydrate Research·A OosterveldA G Voragen
Mar 30, 2001·The Journal of Biological Chemistry·G WardC G Dosoretz
Apr 21, 2001·Journal of Agricultural and Food Chemistry·J H GrabberR D Hatfield
May 23, 2001·Journal of Agricultural and Food Chemistry·G OudgenoegC Laane
Jun 30, 2001·Phytochemistry·M A Bernards, F A Razem
Oct 9, 1964·Biochimica Et Biophysica Acta·S O ANDERSEN

❮ Previous
Next ❯

Citations

Mar 31, 2009·Biotechnology Letters·Kosuke MinamihataMasahiro Goto
Jul 6, 2005·Chemical & Pharmaceutical Bulletin·Hai-Li LiuMasatake Niwa
Jul 13, 2005·The FEBS Journal·Maija-Liisa MattinenCharlotte L Steffensen
May 24, 2014·Bioconjugate Chemistry·Jesper LohseRikke Malene Jørgensen
Apr 22, 2008·Journal of Agricultural and Food Chemistry·Emilia SelinheimoJohanna Buchert
Oct 14, 2004·Journal of Agricultural and Food Chemistry·Carmen G BoeriuAlphons G J Voragen
Jun 19, 2008·Journal of Agricultural and Food Chemistry·Laura FlanderJohanna Buchert

❮ Previous
Next ❯

Related Concepts

Related Feeds

ASBMB Publications

The American Society for Biochemistry and Molecular Biology (ASBMB) includes the Journal of Biological Chemistry, Molecular & Cellular Proteomics, and the Journal of Lipid Research. Discover the latest research from ASBMB here.

Ataxias

Ataxia is a neurological condition characterized by lack of voluntary coordination of muscle movements including loss of coordination, balance, and speech. Discover the latest research on different types of ataxias here.