Lipase-Catalyzed Synthesis of an Epoxy-Functionalized Polyester from the Suberin Monomer <i>cis</i>-9,10-Epoxy-18-hydroxyoctadecanoic Acid

Olsson, Ann; Lindström, Mikael; Iversen, Tommy

doi:10.1021/bm060965w

Cited by 73 publications

(66 citation statements)

References 15 publications

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“…Due to its high content in suberin, birch outer bark has been proposed as a source of monomers, e.g., of ω-hydroxyfatty acids, α,ω-dicarboxylic acids, and homologous mid-chain dihydroxy or epoxy derivatives for production of novel macromolecular materials (Gandini et al, 2006), polyesters (Olsson et al, 2007;Sousa et al, 2007), polyols (Evtiouguina et al, 2000(Evtiouguina et al, , 2002, polyurethanes (Cordeiro et al, 1997(Cordeiro et al, , 1999Evtiouguina et al, 2001) and has also been considered as a source of extractives, namely, of triterpenoids and in particular of betulinol (Pinto et al, 2009). Some patents have already addressed the possibility of using birch bark as a source of chemicals (Krasutsky et al, 2003(Krasutsky et al, , 2005(Krasutsky et al, , 2009).…”

Section: Utilization In Perspectivementioning

confidence: 99%

Cork-Containing Barks—A Review

Leite

Pereira

2017

Front. Mater.

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Tree barks are among the less studied forest products notwithstanding their relevant physiological and protective role in tree functioning. The large diversity in structure and chemical composition of barks makes them a particularly interesting potential source of chemicals and bioproducts, at present valued in the context of biorefineries. One of the valuable components of barks is cork (phellem in anatomy) due to a rather unique set of properties and composition. Cork from the cork oak (Quercus suber) has been extensively studied, mostly because of its economic importance and worldwide utilization of cork products. However, several other species have barks with substantial cork amounts that may constitute additional resources for cork-based bioproducts. This paper makes a review of the tree species that have barks with significant proportion of cork and on the available information regarding the structural and chemical characterization of their bark. A general integrative appraisal of the formation and types of barks and of cork development is also given. The knowledge gaps and the potential interesting research lines are identified and discussed, as well as the utilization perspectives.

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Section: Utilization In Perspectivementioning

confidence: 99%

Cork-Containing Barks—A Review

Leite

Pereira

2017

Front. Mater.

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“…Based on known polymer linkages and in vitro polymerization studies (Olson and Sheares, 2006;Olsson et al, 2007), esterases and lipases represent candidate proteins for polyester condensation . The α/β hydrolase BDG is involved in cutin formation and has been shown to be cell wall-localized (Kurdyukov et al, 2006a).…”

Section: Assembly Of Aliphatic Polyestersmentioning

confidence: 99%

Apoplastic Diffusion Barriers in Arabidopsis

Nawrath

Schreiber

Franke

et al. 2013

The Arabidopsis Book

129

143

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During the development of Arabidopsis and other land plants, diffusion barriers are formed in the apoplast of specialized tissues within a variety of plant organs. While the cuticle of the epidermis is the primary diffusion barrier in the shoot, the Casparian strips and suberin lamellae of the endodermis and the periderm represent the diffusion barriers in the root. Different classes of molecules contribute to the formation of extracellular diffusion barriers in an organ-and tissue-specific manner. Cutin and wax are the major components of the cuticle, lignin forms the early Casparian strip, and suberin is deposited in the stage II endodermis and the periderm. The current status of our understanding of the relationships between the chemical structure, ultrastructure and physiological functions of plant diffusion barriers is discussed. Specific aspects of the synthesis of diffusion barrier components and protocols that can be used for the assessment of barrier function and important barrier properties are also presented.

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“…It has been demonstrated that the presence of functionalizable groups, such as hydroxyl and carboxylate, in polyesters can efficiently increase their hydrophilicity and degradability, plus modulate their mechanical, thermal, chemical, and biological properties (Lecomte et al, 2006;Parrish and Emrick, 2006;Williams, 2007). Within the new group of degradable polymers, various types of aliphatic polyesters films have been described (Bayer et al, 2004;Benitez et al, 2004;Olsson et al, 2007;Heredia-Guerrero et al, 2009;Quinzler and Mecking, 2010;Stempfle et al, 2014;Benítez et al, 2015). Between them, successful polycondensation reactions have been achieved using titanium alkoxides as catalyst to afford the corresponding longchain aliphatic polyesters (Quinzler and Mecking, 2010;Stempfle et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

“…Even when long-chain polyhydroxyesters (C16-C20) are present in nature in the form of the plant biopolymer cutin, its monomeric complexity makes difficult to get and use it as natural polyester for commercial source of "green" chemicals (Olsson et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Polymerization of 10,16-Dihydroxyhexadecanoic Acid, Main Monomer of Tomato Cuticle, Using the Lewis Acidic Ionic Liquid Choline Chloride·2ZnCl2

et al. 2015

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10,16-Dihydroxyhexadecanoic acid, main monomer of the tomato cuticle obtained from agroresidual wastes, was polymerized using ionic liquid (choline chloride·2ZnCl 2 ) as catalyst at three different temperatures (80, 90, and 100°C). The resulting polyesters obtained under these conditions were insoluble in most of the organic solvents and showed different physicochemical properties. While at 80°C, polymers were obtained as powder, and at higher temperature, they were found in viscous consistency. According to the cross polarization magic angle spinning nuclear magnetic resonance and Fourier transform infrared spectroscopy attenuated total reflectance analysis, polymers showed a linear structure with an increasing degree of esterification in position C-10. Polyesters were analyzed by means of differential scanning calorimetry, atomic force microscopy, and X-ray diffraction (small-and wide-angle scattering) techniques.

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Lipase-Catalyzed Synthesis of an Epoxy-Functionalized Polyester from the Suberin Monomer cis-9,10-Epoxy-18-hydroxyoctadecanoic Acid

Cited by 73 publications

References 15 publications

Cork-Containing Barks—A Review

Cork-Containing Barks—A Review

Apoplastic Diffusion Barriers in Arabidopsis

Polymerization of 10,16-Dihydroxyhexadecanoic Acid, Main Monomer of Tomato Cuticle, Using the Lewis Acidic Ionic Liquid Choline Chloride·2ZnCl2

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