4.5 Article

Use of ionic liquid for the enzyme-catalyzed polymerization of phenols

Journal

POLYMERS FOR ADVANCED TECHNOLOGIES
Volume 21, Issue 6, Pages 454-456

Publisher

WILEY
DOI: 10.1002/pat.1452

Keywords

enzyme-catalyst; horseradish peroxidase; polyphenol; ionic liquids

Funding

  1. CONACyT-Mexico [48641]
  2. DGAPA (UNAM) [IN200109-3]

Ask authors/readers for more resources

Ionic liquid and buffer mixture media are first reported in the peroxidase-catalyzed polymerization of phenol. Yield of 100% with molecular weights of 7000 KDa, as assessed by size-exclusion chromatography (SEC), were attained using 1-butyl-3-methylimidazolium tetrafluoroborate-buffer mixtures with added hydrogen peroxide. The simplicity of the process and the low vapor pressure of the solvent media allow an eco-friendly alternative to the general synthesis of polyphenolic-type biopolymers. Evidence for the consequent polyphenol (PPO) was obtained from solid-state C-13 cross-polarization magic angle spinning (CP-MAS) NMR spectroscopy and FT-IR. Copyright (C) 2009 John Wiley & Sons, Ltd.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.5
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Cell Biology

The enzymatic poly(gallic acid) reduces pro-inflammatory cytokines in vitro, a potential application in inflammatory diseases

Yessica Zamudio-Cuevas, Marco A. Andonegui-Elguera, Ariadna Aparicio-Juarez, Edson Aguillon-Solis, Karina Martinez-Flores, Erika Ruvalcaba-Paredes, Cristina Velasquillo-Martinez, Clemente Ibarra, Valentin Martinez-Lopez, Marwin Gutierrez, Roeb Garcia-Arrazola, Carmen G. Hernandez-Valencia, Alejandra Romero-Montero, Miguel A. Hernandez-Valdepena, Miquel Gimeno, Roberto Sanchez-Sanchez

Summary: Studies have shown that PGAL can reduce the release of pro-inflammatory cytokines, decrease cell proliferation and adhesion, potentially offering therapeutic benefits for certain inflammatory diseases.

INFLAMMATION (2021)

Article Materials Science, Biomaterials

Antioxidant and antimicrobial material by grafting of L-arginine onto enzymatic poly(gallic acid)

Miguel A. Hernandez-Valdepena, Carmen G. Hernandez-Valencia, Pablo Labra-Vazquez, Carmen Wacher, Gloria Diaz-Ruiz, Alfredo Vazquez, Jose Pedraza-Chaverri, Keiko Shirai, Alberto Rosas-Aburto, Eduardo Vivaldo-Lima, Eduardo Barzana, Romina Rodriguez-Sonoja, Miquel Gimeno

Summary: Microwave-mediated grafting of L-Arginine onto naturally derived and stable multiradical poly(gallic acid) has been achieved successfully. This polymeric material showed no adverse effects on human cells and preserved its antioxidant properties, while also exhibiting antimicrobial activity against various bacterial strains. The mechanism of bacterial inhibition was related to the formation of porous channels on the membrane, influenced by the helical secondary structure of the polymer and the amino acid guanidyl moieties interacting with bacterial membranes.

MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS (2021)

Article Energy & Fuels

Supercritical carbon dioxide explosion on blue agave bagasse to enhance enzymatic digestibility

Armando Navarro, Carmina Montiel, Jesus Gracia-Fadrique, Alberto Tecante, Eduardo Barzana

Summary: Supercritical carbon dioxide (SCCO2) pretreatment of blue agave bagasse (BAB) enhances enzymatic hydrolysis (EH) to simple sugars for bioethanol fermentation.

BIOMASS CONVERSION AND BIOREFINERY (2023)

Article Engineering, Chemical

An Experimental and Modeling Study on the Pretreatment and Alkaline Hydrolysis of Blue Agave Bagasse in Twin-Screw Extruders

Juan Carlos Morales-Huerta, Oscar Hernandez-Melendez, Martin Guillermo Hernandez-Luna, Octavio Manero, Eduardo Barzana, Eduardo Vivaldo-Lima

Summary: The study used a mathematical model to analyze the de-construction and degradation of blue agave bagasse in a laboratory-scale extruder. Experimental results showed that NaOH concentration, residence time, and temperature play key roles in the extraction of cellulose and hemicelluloses. The model demonstrated good agreement with experimental data, suggesting its potential for industrial process analysis and scaling up in the future.

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH (2021)

Article Cell Biology

Anti-inflammatory and Antioxidant Effect of Poly-gallic Acid (PGAL) in an In Vitro Model of Synovitis Induced by Monosodium Urate Crystals

Yessica Zamudio-Cuevas, Valentin Martinez-Lopez, Ivan Alejandro Lujan-Juarez, Nathalie Montano-Armendariz, Karina Martinez-Flores, Javier Fernandez-Torres, Miquel Gimeno, Roberto Sanchez-Sanchez

Summary: Gout is a chronic and degenerative disease caused by the crystalline deposit of monosodium urate, and poly-gallic acid has been found to be effective in reducing MSU-induced inflammation and oxidative stress.

INFLAMMATION (2022)

Article Cell Biology

Boar semen cryopreserved with trehalose-containing liposomes: disaccharide determination and rheological behaviour

Claudia Denisse Mendoza-Viveros, Oscar Gutierrez-Perez, Maria Josefa Bernad-Bernad, Luis Medina-Torres, Minerva Monroy-Barreto, Miquel Gimeno, Maria Elena Trujillo-Ortega

Summary: The use of liposomes with trehalose appears to be a promising option for boar semen cryopreservation, with a marked effect on rheological properties. The proposed HPLC-ELSD method was effective for measuring trehalose in cryopreserved cell samples.

ZYGOTE (2022)

Article Biotechnology & Applied Microbiology

Protease-catalyzed synthesis of a-poly-L-Lysine and amphiphilic poly(L-lysine-co-L-phenylalanine) in a neat non-toxic organic solvent

Angel Espinoza-Gonzalez, Carmen Hernandez-Valencia, Luis Cedeno-Caero, Roberto Sanchez-Sanchez, Carmina Montiel, Miquel Gimeno

Summary: Subtilisin Carlsberg, an alkaline protease from Bacillus licheniformis, can catalyze the synthesis of high molecular weight cationic alpha-poly-L-lysine and amphiphilic poly(alpha-L-lysine-co-L-phenylalanine) in organic solvent. The reaction is conducted in hydrophobic non-toxic 1,1,1,2-tetrafluoroethane solvent, and the low water environment limits hydrolysis of the peptide chains. The organic compressed fluid used in the reaction has low-pressure requirements and evaporates completely after the reaction, leaving no solvent residues. The resulting polypeptides show no cytotoxicity in human cells.

BIOPROCESS AND BIOSYSTEMS ENGINEERING (2023)

Article Polymer Science

Removal of Heavy Metal Ions from Wastewater with Poly-e-Caprolactone-Reinforced Chitosan Composite

Manuel E. Martinez, Jose Rene Rangel-Mendez, Miquel Gimeno, Alberto Tecante, Gretchen T. Lapidus, Keiko Shirai

Summary: A chitosan reinforced with poly-epsilon-caprolactone thermoplastic composite was prepared and characterized in this study. The results showed that the material had high adsorption equilibrium capacities for Zn(II), Cu(II), Fe(II), and Al(III), and had minimal mass loss during the adsorption-desorption process.

POLYMERS (2022)

Article Food Science & Technology

Supercritical CO2 Extraction of oil from Chan (Hyptis suaveolens (L.) Poit) Seeds and its Physicochemical Characterization, Spectroscopy and Nutritional Analysis

Maria Dolores Diaz-Cervantes, Emma Gloria Ramos-Ramirez, Miquel Gimeno-Seco, Juan Alfredo Salazar-Montoya

Summary: The study aimed to optimize the extraction of chan seed oil using supercritical fluid and response surface methodology, and evaluate its physicochemical properties and quality. The optimal extraction conditions were determined to be 450 bar, 80 degrees C, and 193 min, resulting in a yield of 9.21% and recovery of 62.36%. The oil exhibited good stability and high content of omega 3, 6, and 9 fatty acids.

FOOD ANALYTICAL METHODS (2023)

Article Chemistry, Applied

Benign and straightforward synthesis of lignan-type dimers using crude peroxidase from red radish (Raphanus sativus var sativus)

A. Navarro, M. Gimeno, S. Alatorre-Santamaria, A. Navarro-Ocana

Summary: In this study, it was found that the enzymatic extract of Raphanus sativus var sativus exhibited peroxidase activity and catalyzed oxidative coupling of phenols, resulting in the formation of vanilloid and alkyl ester dimers.

REVISTA MEXICANA DE INGENIERIA QUIMICA (2022)

Article Materials Science, Biomaterials

Enzymatic poly(gallic acid)-grafted ?-L-lysine inhibits Staphylococcus aureus and Escherichia coli strains with no cytotoxicity for human cells

Carmen G. Hernandez-Valencia, Miguel A. Hernandez-Valdepena, Alfredo Vazquez, Luis Cedeno-Caero, Jose Pedraza-Chaverri, Roberto Sanchez-Sanchez, Miquel Gimeno

Summary: The poly(gallic acid) grafted with -L-Lysine (LL) exhibits excellent antimicrobial activity against gram-positive Staphylococcus aureus and gram-negative Escherichia coli strains. The interaction between the positive charged polymer and the negatively charged bacterial membranes suggests a mechanism of pore-formation and translocation. Furthermore, the LL hybridized polymer shows antioxidant activity, high hemolysis concentration, and no cytotoxicity on human dermal fibroblasts, making it a promising antimicrobial material with potential cell preservation effects.

BIOMATERIALS ADVANCES (2022)

Article Cell Biology

Anti-inflammatory and Antioxidant Effect of Poly-gallic Acid (PGAL) in an In Vitro Model of Synovitis Induced by Monosodium Urate Crystals

Yessica Zamudio-Cuevas, Valentin Martinez-Lopez, Ivan Alejandro Lujan-Juarez, Nathalie Montano-Armendariz, Karina Martinez-Flores, Javier Fernandez-Torres, Miquel Gimeno, Roberto Sanchez-Sanchez

Summary: This study evaluated the effect of poly-gallic acid (PGAL) in an in vitro model of oxidation and synovial inflammation induced by monosodium urate (MSU) crystals. The results showed that PGAL reduced cell death and vesicle generation, decreased oxidative stress, and inhibited the inflammatory response. PGAL exhibited a cytoprotective effect against MSU-induced damage in synoviocytes.

INFLAMMATION (2022)

Article Food Science & Technology

Extraction of Essential Oil from Waste Grapefruit Peel Using a Pilot-Scale Twin-Screw Extruder

Lazaro Gabriel Trujillo-Juarez, Oscar Hernandez-Melendez, Miguel Gimeno, Jesus Gracia-Fadrique, Eduardo Barzana

Summary: Citrus peels are a rich source of essential oils (EOs), which are widely used in the food, cosmetics, and pharmaceutical industries. This study proposed a method for extracting EOs from grapefruit peel using a pilot-scale twin-screw extruder, showing high productivity and energy efficiency. The produced EOs met international quality standards and can be used for commercial purposes.

ACS FOOD SCIENCE & TECHNOLOGY (2021)

Article Polymer Science

MEH-PPV/SBS composite films: Localization and luminescence properties of conductive polymers with microphase separation

Zhongming Yuan, Hiroko Yamamoto, Shinji Kanehashi, Takeshi Shimomura

Summary: This study reports the synthesis of a flexible light-emitting polymer film using a solution blending method. The selective positioning of MEH-PPV molecules in the PS phase of the film was confirmed. The film exhibited a nanometer-scale luminescent domain with low aggregation quenching and showed good elastomeric characteristics.

POLYMERS FOR ADVANCED TECHNOLOGIES (2024)