Radical Coupling Reactions in Lignin Synthesis: A Density Functional Theory Study

2012 ◽  
Vol 116 (16) ◽  
pp. 4760-4768 ◽  
Author(s):  
Amandeep K. Sangha ◽  
Jerry M. Parks ◽  
Robert F. Standaert ◽  
Angela Ziebell ◽  
Mark Davis ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Coupling Reactions ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Radical Coupling ◽  
Lignin Synthesis

scholarly journals Radical coupling reactions of piceatannol and monolignols: A density functional theory study

2019 ◽  
Vol 164 ◽  
pp. 12-23 ◽  
Author(s):  
Thomas Elder ◽  
José Carlos del Río ◽  
John Ralph ◽  
Jorge Rencoret ◽  
Hoon Kim ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Coupling Reactions ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Radical Coupling

scholarly journals Radical Coupling Reactions of Hydroxystilbene Glucosides and Coniferyl Alcohol: A Density Functional Theory Study

2021 ◽  
Vol 12 ◽  
Author(s):  
Thomas Elder ◽  
Jorge Rencoret ◽  
José C. del Río ◽  
Hoon Kim ◽  
John Ralph
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Biosynthetic Pathway ◽  
Cross Coupling ◽  
Coniferyl Alcohol ◽  
Coupling Reactions ◽  
Functional Theory ◽  
Radical Coupling ◽  
Synthetic Models

The monolignols, p-coumaryl, coniferyl, and sinapyl alcohol, arise from the general phenylpropanoid biosynthetic pathway. Increasingly, however, authentic lignin monomers derived from outside this process are being identified and found to be fully incorporated into the lignin polymer. Among them, hydroxystilbene glucosides, which are produced through a hybrid process that combines the phenylpropanoid and acetate/malonate pathways, have been experimentally detected in the bark lignin of Norway spruce (Picea abies). Several interunit linkages have been identified and proposed to occur through homo-coupling of the hydroxystilbene glucosides and their cross-coupling with coniferyl alcohol. In the current work, the thermodynamics of these coupling modes and subsequent rearomatization reactions have been evaluated by the application of density functional theory (DFT) calculations. The objective of this paper is to determine favorable coupling and cross-coupling modes to help explain the experimental observations and attempt to predict other favorable pathways that might be further elucidated via in vitro polymerization aided by synthetic models and detailed structural studies.

Sign in / Sign up

Export Citation Format

Share Document