Dehydrogenative Polymerization of Coniferyl Alcohol in Artificial Polysaccharides Matrices: Effects of Xylan on the Polymerization

2015 ◽  
Vol 63 (18) ◽  
pp. 4613-4620 ◽  
Author(s):  
Qiang Li ◽  
Keiichi Koda ◽  
Arata Yoshinaga ◽  
Keiji Takabe ◽  
Masatsugu Shimomura ◽  
...  
Keyword(s):  
Coniferyl Alcohol ◽  
Dehydrogenative Polymerization

Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 2: Horseradish peroxidase-catalyzed dehydrogenative polymerization of isoconiferin

Holzforschung ◽  
2006 ◽  
Vol 60 (5) ◽  
pp. 513-518 ◽  
Author(s):  
Yuki Tobimatsu ◽  
Toshiyuki Takano ◽  
Hiroshi Kamitakahara ◽  
Fumiaki Nakatsubo
Keyword(s):  
Horseradish Peroxidase ◽  
Water Solubility ◽  
Homogeneous System ◽  
Degree Of Polymerization ◽  
Coniferyl Alcohol ◽  
Water Soluble ◽  
Optimum Conditions ◽  
Spectroscopic Analyses ◽  
Dehydrogenation Polymer ◽  
Dehydrogenative Polymerization

Abstract Dehydrogenative polymerization of isoconiferin (IC; coniferyl alcohol γ-O-β-D-glucopyranoside) catalyzed by horseradish peroxidase (HRP) was carried out. The polymerization of IC proceeded in a homogeneous system, resulting in a water-soluble dehydrogenation polymer (IC-DHP). The degree of polymerization (DP) of IC-DHP was significantly higher than that of a standard dehydrogenative polymer (CA-DHP) obtained from coniferyl alcohol (CA) in a heterogeneous system. Under optimum conditions, the DP of IC-DHP was 44 (M n=1.5×104), whereas that for CA-DHP was only 11 (M n=3.0×103, as acetate). Spectroscopic analyses confirmed that IC-DHP has a lignin-like structure containing D-glucose moieties attached to the lignin side-chains. The D-glucose unit introduced into γ-O position of CA essentially influenced the water solubility and molecular mass of the resulting DHP.

Generation of lignin polymer models via dehydrogenative polymerization of coniferyl alcohol and syringyl alcohol via several plant peroxidases involved in lignification and analysis of the resulting DHPs by MALDI-TOF analysis

Holzforschung ◽  
2018 ◽  
Vol 72 (4) ◽  
pp. 267-274 ◽  
Author(s):  
Jun Shigeto ◽  
Hiroki Honjo ◽  
Koki Fujita ◽  
Yuji Tsutsumi
Keyword(s):  
Cell Wall ◽  
Horseradish Peroxidase ◽  
Molecular Size ◽  
Coniferyl Alcohol ◽  
Populus Alba ◽  
Polymer Formation ◽  
Polymer Models ◽  
Plant Peroxidases ◽  
Molecular Size Distribution ◽  
Dehydrogenative Polymerization

AbstractThe mechanism of lignin dehydrogenative polymerization (DHP), made by means of horseradish peroxidase (HRP), was studied in comparison with other plant peroxidases. Interestingly, HRP is efficient for guaiacyl type polymer formation (G-DHPs), but is not efficient in the case of syringyl type DHPs (S-DHPs). It was previously demonstrated that lignification-relatedArabidopsisthalianaperoxidases, AtPrx2, AtPrx25 and AtPrx71, and cationic cell-wall-bound peroxidase (CWPO-C) fromPopulus albaare successful to oxidize syringyl- and guaiacyl-type monomers and larger lignin-like molecules. This is the reason why in the present study the DHP formation by means of these recombinant peroxidases was tested, and all these enzymes were successful for formation of both G-DHP and S-DHP in acceptable yields. CWPO-C led to S-DHP molecular size distribution similar to that of isolated lignins.

Radical transfer system in the enzymatic dehydrogenative polymerization (DHP formation) of coniferyl alcohol (CA) and three dilignols

Holzforschung ◽  
2019 ◽  
Vol 73 (2) ◽  
pp. 189-195 ◽  
Author(s):  
Yasuyuki Matsushita ◽  
Masaya Okayama ◽  
Dan Aoki ◽  
Sachie Yagami ◽  
Kazuhiko Fukushima
Keyword(s):  
Molecular Weight ◽  
Reaction Kinetics ◽  
Consumption Rate ◽  
Coniferyl Alcohol ◽  
Clear Picture ◽  
Transfer System ◽  
Radical Transfer ◽  
Dehydrodiconiferyl Alcohol ◽  
Dehydrogenative Polymerization

Abstract No clear picture has yet been elaborated concerning the mechanism of lignin growth, and thus this topic is the focus of the present paper. Namely, the enzymatic dehydrogenative polymerization (DHP formation) of coniferyl alcohol (CA, as a monolignol) and three dilignols and their reaction kinetics were investigated. The dilignols [guaiacylglycerol-β-coniferyl ether (IβO4), dehydrodiconiferyl alcohol (IIβ5), and pinoresinol (IIIββ)] and CA as a monolignol [(3-OCD3)-coniferyl alcohol (CAOCD3)] were synthesized and subjected to enzymatic DHP formation. The dilignol derived from CAOCD3 could be identified by its higher molecular weight in comparison with the starting dilignols (IβO4, IIβ5, and IIIββ). Based on the observed consumption rate of the CA and its dilignols, it was proposed that a radical transfer system exists between the dilignols, which is generated from the CA and the starting substrates.

Monolignol dehydrogenative polymerization in vitro in the presence of dioxane and a methylated β-β′ dimer model compound

Holzforschung ◽  
2008 ◽  
Vol 62 (5) ◽  
Author(s):  
Anders Holmgren ◽  
Liming Zhang ◽  
Gunnar Henriksson
Keyword(s):  
Model Compound ◽  
Coniferyl Alcohol ◽  
Enzymatic Oxidation ◽  
High Solubility ◽  
Dimer Model ◽  
Homogeneous Polymerization ◽  
Lignin Polymerization ◽  
C Nmr ◽  
Dehydrogenative Polymerization

Abstract Lignin formation is believed to occur by polymerization of resonance-stabilized monolignol radicals formed by enzymatic oxidation. Recently, different hypotheses suggested that lignin polymerization is influenced by surfaces in the cell wall which can be polysaccharides or proteins. The latter is called the proteinaceous dirigent sites/template polymerization hypothesis. According to another hypothesis, lignin itself is believed to act as a template and replicate its primary structure. In this work, dehydrogenative polymerization (DHP) of the lignin precursor coniferyl alcohol was performed in vitro in the presence and absence of pinoresinol dimethyl ether (a β-β′ dimer model). Another peculiarity of the experiments was the presence of dioxane which afforded a high solubility of the reactants. The question was whether the presence of β-β′ dimer model would change the structure of the DHP formed. The DHPs were analyzed by quantitative 13C NMR, GC-FID, and GC-MS. The dimer model as a template in the homogeneous polymerization state (in solution) did not influence the DHP structure.

Effects of a Biologically Relevant Antioxidant on the Dehydrogenative Polymerization of Coniferyl Alcohol

2008 ◽  
Vol 9 (12) ◽  
pp. 3378-3382 ◽  
Author(s):  
Anders Holmgren ◽  
Gunnar Henriksson ◽  
Liming Zhang
Keyword(s):  
Coniferyl Alcohol ◽  
Biologically Relevant ◽  
Dehydrogenative Polymerization

scholarly journals Oxidation of coniferyl alcohol by cell wall peroxidases at the expense of indole-3-acetic acid and O2

FEBS Letters ◽  
1990 ◽  
Vol 276 (1-2) ◽  
pp. 127-130 ◽  
Author(s):  
María A. Ferrer ◽  
María A. Pedreño ◽  
Romualdo Muñoz ◽  
A.Ros Barceló
Keyword(s):  
Cell Wall ◽  
Acetic Acid ◽  
Coniferyl Alcohol ◽  
Indole 3 Acetic Acid

Improving bioconversion of eugenol to coniferyl alcohol by constitutive promoters in Escherichia coli

2021 ◽  
Vol 168 ◽  
pp. 107953
Author(s):  
Hengrui Zhou ◽  
Song Gao ◽  
Weizhu Zeng ◽  
Jingwen Zhou
Keyword(s):  
Escherichia Coli ◽  
Coniferyl Alcohol

Synergistic Experimental and Computational Approach Identifies Novel Strategies for PHB Overproduction

2021 ◽  
Author(s):  
Adil Alsiyabi ◽  
Brandi Brown ◽  
Cheryl Immethun ◽  
Mark Wilkins ◽  
Rajib Saha
Keyword(s):  
Engineering Design ◽  
Rhodopseudomonas Palustris ◽  
Maximum Yield ◽  
Computational Approach ◽  
Coniferyl Alcohol ◽  
Breakdown Product ◽  
Design Strategies ◽  
Metabolic Factors ◽  
Model Driven ◽  
Phb Production

Abstract Polyhydroxybutyrate (PHB) is a sustainable bioplastic produced by bacteria that is a potential replacement for conventional plastics. This study delivers an integrated experimental and computational modeling approach to decipher metabolic factors controlling PHB production and offers engineering design strategies to boost production. In the metabolically robust Rhodopseudomonas palustris CGA009, PHB production significantly increased when grown on the carbon- and electron-rich lignin breakdown product p-coumarate (C9H8O3) compared to acetate when the same amount of carbon was supplied. However, the maximum yield did not improve further when grown on coniferyl alcohol (C10H12O3). In order to obtain a systems-level understanding of factors driving PHB yield, a model-driven investigation was performed. The model yielded several engineering design strategies including utilizing reduced, high molecular weight substrates that bypass the thiolase reaction. Overall, these findings uncover key parameters controlling PHB production and design strategies that can potentially be expanded to any bacterium for optimizing PHB production.

Sign in / Sign up

Export Citation Format

Share Document