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Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins

(2010) PLANT PHYSIOLOGY. 153(2). p.569-579
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Abstract
Caffeic acid O-methyltransferase (COMT) is a bifunctional enzyme that methylates the 5- and 3-hydroxyl positions on the aromatic ring of monolignol precursors, with a preference for 5-hydroxyconiferaldehyde, on the way to producing sinapyl alcohol. Lignins in COMT-deficient plants contain benzodioxane substructures due to the incorporation of 5-hydroxyconiferyl alcohol (5-OH-CA), as a monomer, into the lignin polymer. The derivatization followed by reductive cleavage method can be used to detect and determine benzodioxane structures because of their total survival under this degradation method. Moreover, partial sequencing information for 5-OH-CA incorporation into lignin can be derived from detection or isolation and structural analysis of the resulting benzodioxane products. Results from a modified derivatization followed by reductive cleavage analysis of COMT-deficient lignins provide evidence that 5-OH-CA cross couples (at its beta-position) with syringyl and guaiacyl units (at their O-4-positions) in the growing lignin polymer and then either coniferyl or sinapyl alcohol, or another 5-hydroxyconiferyl monomer, adds to the resulting 5-hydroxyguaiacyl terminus, producing the benzodioxane. This new terminus may also become etherified by coupling with further monolignols, incorporating the 5-OH-CA integrally into the lignin structure.
Keywords
IMPACT, REVEALS, CLEAVAGE, PLANTS, TRIMERS, DFRC METHOD, OLIGOLIGNOLS, TRANSGENIC POPLARS, NMR

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Chicago
Lu, Fachuang, Jane M Marita, Catherine Lapierre, Lise Jouanin, Kris Morreel, Wout Boerjan, and John Ralph. 2010. “Sequencing Around 5-hydroxyconiferyl Alcohol-derived Units in Caffeic Acid O-methyltransferase-deficient Poplar Lignins.” Plant Physiology 153 (2): 569–579.
APA
Lu, F., Marita, J. M., Lapierre, C., Jouanin, L., Morreel, K., Boerjan, W., & Ralph, J. (2010). Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins. PLANT PHYSIOLOGY, 153(2), 569–579.
Vancouver
1.
Lu F, Marita JM, Lapierre C, Jouanin L, Morreel K, Boerjan W, et al. Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins. PLANT PHYSIOLOGY. 2010;153(2):569–79.
MLA
Lu, Fachuang, Jane M Marita, Catherine Lapierre, et al. “Sequencing Around 5-hydroxyconiferyl Alcohol-derived Units in Caffeic Acid O-methyltransferase-deficient Poplar Lignins.” PLANT PHYSIOLOGY 153.2 (2010): 569–579. Print.
@article{1038812,
  abstract     = {Caffeic acid O-methyltransferase (COMT) is a bifunctional enzyme that methylates the 5- and 3-hydroxyl positions on the aromatic ring of monolignol precursors, with a preference for 5-hydroxyconiferaldehyde, on the way to producing sinapyl alcohol. Lignins in COMT-deficient plants contain benzodioxane substructures due to the incorporation of 5-hydroxyconiferyl alcohol (5-OH-CA), as a monomer, into the lignin polymer. The derivatization followed by reductive cleavage method can be used to detect and determine benzodioxane structures because of their total survival under this degradation method. Moreover, partial sequencing information for 5-OH-CA incorporation into lignin can be derived from detection or isolation and structural analysis of the resulting benzodioxane products. Results from a modified derivatization followed by reductive cleavage analysis of COMT-deficient lignins provide evidence that 5-OH-CA cross couples (at its beta-position) with syringyl and guaiacyl units (at their O-4-positions) in the growing lignin polymer and then either coniferyl or sinapyl alcohol, or another 5-hydroxyconiferyl monomer, adds to the resulting 5-hydroxyguaiacyl terminus, producing the benzodioxane. This new terminus may also become etherified by coupling with further monolignols, incorporating the 5-OH-CA integrally into the lignin structure.},
  author       = {Lu, Fachuang and Marita, Jane M and Lapierre, Catherine and Jouanin, Lise and Morreel, Kris and Boerjan, Wout and Ralph, John},
  issn         = {0032-0889},
  journal      = {PLANT PHYSIOLOGY},
  keyword      = {IMPACT,REVEALS,CLEAVAGE,PLANTS,TRIMERS,DFRC METHOD,OLIGOLIGNOLS,TRANSGENIC POPLARS,NMR},
  language     = {eng},
  number       = {2},
  pages        = {569--579},
  title        = {Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins},
  url          = {http://dx.doi.org/10.1104/pp.110.154278},
  volume       = {153},
  year         = {2010},
}

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