Covalent bond formation between amino acids and lignin: Cross-coupling between proteins and lignin

Fang Cong, Brett G. Diehl, Joseph Lee Hill, Nicole Brown, Ming Tien

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The present study characterized the products formed from the reaction of amino acids and in turn, proteins, with lignin resulting in cross-coupling. When added to reaction mixtures containing coniferyl alcohol, horseradish peroxidase and H2O2, three amino acids (Cys, Tyr, and Thr) are able to form adducts. The low molecular weight products were analyzed by HPLC and from each reaction mixture, one product was isolated and analyzed by LC/MS. LC/MS results are consistent with bond formation between the polar side-chain of these amino acids with Cα. These results are consistent with the cross-coupling of Cys, Tyr and Thr through a quinone methide intermediate. In addition to the free amino acids, it was found that the cross-coupling of proteins with protolignin through Cys or Tyr residues. The findings provide a mechanism by which proteins and lignin can cross-couple in the plant cell wall.

Original languageEnglish (US)
Pages (from-to)449-456
Number of pages8
JournalPhytochemistry
Volume96
DOIs
StatePublished - Jan 1 2013

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Covalent bonds
Lignin
lignin
Amino Acids
amino acids
coniferyl alcohol
Proteins
proteins
quinones
free amino acids
peroxidase
Plant Cells
Horseradish Peroxidase
cell walls
Cell Wall
molecular weight
Molecular Weight
Molecular weight
High Pressure Liquid Chromatography

All Science Journal Classification (ASJC) codes

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Horticulture

Cite this

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Covalent bond formation between amino acids and lignin : Cross-coupling between proteins and lignin. / Cong, Fang; Diehl, Brett G.; Hill, Joseph Lee; Brown, Nicole; Tien, Ming.

In: Phytochemistry, Vol. 96, 01.01.2013, p. 449-456.

Research output: Contribution to journalArticle

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T1 - Covalent bond formation between amino acids and lignin

T2 - Cross-coupling between proteins and lignin

AU - Cong, Fang

AU - Diehl, Brett G.

AU - Hill, Joseph Lee

AU - Brown, Nicole

AU - Tien, Ming

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