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 language | English (US) |
|---|---|
| Pages (from-to) | 449-456 |
| Number of pages | 8 |
| Journal | Phytochemistry |
| Volume | 96 |
| DOIs | |
| State | Published - Jan 1 2013 |
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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 journal › Article
TY - JOUR
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
PY - 2013/1/1
Y1 - 2013/1/1
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=84888605523&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2013.09.012
DO - 10.1016/j.phytochem.2013.09.012
M3 - Article
C2 - 24099658
AN - SCOPUS:84888605523
VL - 96
SP - 449
EP - 456
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
ER -