Synthesis of xylan carbonates – An approach towards reactive polysaccharide derivatives showing self-assembling into nanoparticles

Gericke, Martin; Gabriel, Lars; Geitel, Katja; Benndorf, Stefan; Trivedi, Poonam; Fardim, Pedro; Heinze, Thomas

doi:10.1016/j.carbpol.2018.03.083

Cited by 23 publications

(20 citation statements)

References 28 publications

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“…[ 154 ] A strong influence of the PS backbone on the nano‐selfassembling has also been observed for PS phenyl carbonates. [ 155 ] Xylan phenyl carbonates formed well defined PS‐NP with a size of about 160 nm by dialysis whereas the corresponding cellulose derivatives only formed macroscopic aggregates.…”

Section: Polysaccharide‐based Nanoparticlesmentioning

confidence: 99%

Nanoparticles Based on Hydrophobic Polysaccharide Derivatives—Formation Principles, Characterization Techniques, and Biomedical Applications

Gericke

Schulze

Heinze

2020

Macromolecular Bioscience

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Polysaccharide (PS) nanoparticles (NP) are fascinating materials that combine huge application potential with the unique beneficial features of natural biopolymers. Different types of PS‐NP can be distinguished depending on the basic preparation principles (top‐down vs bottom‐up vs coating of nanomaterials) and the material from which they are obtained (native PS vs chemically modified PS derivatives vs nanocomposites). This review provides a comprehensive overview of an approach towards PS‐NP that has gained rapidly increasing interest within the last decade; the nanoself‐assembling of hydrophobic PS derivatives. This facile process is easy to perform and offers a broad structural diversity in terms of the PS backbone and the additional functionalities that can be introduced. Fundamental principles of different NP preparation techniques along with useful characterization methods are presented in this work. A comprehensive summary of PS‐NP prepared by different techniques and with various PS backbones and types/amounts of hydrophobic substituents is given. The intention is to demonstrate how different parameters determine the size, size distribution, and zeta‐potential of the particles. Moreover, application trends in biomedical areas are highlighted in which tailored functional PS‐NP are evaluated and constantly developed further.

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Section: Polysaccharide‐based Nanoparticlesmentioning

confidence: 99%

Nanoparticles Based on Hydrophobic Polysaccharide Derivatives—Formation Principles, Characterization Techniques, and Biomedical Applications

Gericke

Schulze

Heinze

2020

Macromolecular Bioscience

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“…PS derivatives with phenyl carbonate substituents derived from cellulose and xylan were found to be very versatile intermediates that can react with a broad variety of molecules that carry nucleophilic amino groups [ 15 , 16 ]. At the same time, nano self-assembling of some PS derivatives with carbonate substituents (aryl and alkyl) has been reported [ 17 , 18 ]. It is reasonable to assume that carbonate substituents can fulfill a dual purpose to provide an easy access to reactive PS-NP.…”

Section: Introductionmentioning

confidence: 99%

Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates

et al. 2021

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Polysaccharide (PS) based nanoparticles (NP) are of great interest for biomedical applications. A key challenge in this regard is the functionalization of these nanomaterials. The aim of the present work was the development of reactive PS-NP that can be coupled with an amino group containing compounds under mild aqueous conditions. A series of cellulose phenyl carbonates (CPC) and xylan phenyl carbonates (XPC) with variable degrees of substitution (DS) was obtained by homogeneous synthesis. The preparation of PS-NP by self-assembling of these hydrophobic derivatives was studied comprehensively. While CPC mostly formed macroscopic aggregates, XPC formed well-defined spherical NP with diameters around 100 to 200 nm that showed a pronounced long-term stability in water against both particle aggregation as well as cleavage of phenyl carbonate moieties. Using an amino group functionalized dye it was demonstrated that the novel XPC-NP are reactive towards amines. A simple coupling procedure was established that enables direct functionalization of the reactive NP in an aqueous dispersion. Finally, it was demonstrated that dye functionalized XPC-NP are non-cytotoxic and can be employed in advanced biomedical applications.

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“…It is also unclear whether the abovementioned phenotype would differ if IRX10 was downregulated. Despite being a contributor to recalcitrance, xylan is a valuable bioproduct of cellulose pulping that can be used for various applications such as hydrogels, nanoparticles and 3D printing bioinks (Gericke et al, 2018; Li and Su, 2018; Xu et al, 2018). It also has dietary value (Huang et al, 2018) as well as being a source of value added products such as acetone, xylitol, xylooligosaccharides, furfural, hydroxymethylfurfural, levulinic acid, polylactic acid and ethanol (Parajó et al, 1997; Zhao et al, 2007; Binder et al, 2010; Deutschmann and Dekker, 2012; Gürbüz et al, 2012; Li et al, 2013; Zhao et al, 2013; Lama et al, 2014; Figure 1).…”

Section: Novel Biotechnology Strategiesmentioning

confidence: 99%

“…Therefore, it could be possible to engineer microfibril angles required by specific industries or biorefinery applications by altering FLA expression patterns. Pectin and xylan can be converted into various value added products through biorefining (Deutschmann and Dekker, 2012; Gürbüz et al, 2012; Xiao and Anderson, 2013; Gericke et al, 2018; Figure 1), overexpressing IRX8 lead to increase in both of these biopolymers (Biswal et al, 2018). However, this plant also displayed increased biomass recalcitrance and decreased growth, if these undesirable traits could be alleviated, the IRX8 overexpressor may have biorefinery applications.…”

Section: Novel Biotechnology Strategiesmentioning

confidence: 99%

Xylan in the Middle: Understanding Xylan Biosynthesis and Its Metabolic Dependencies Toward Improving Wood Fiber for Industrial Processing

et al. 2019

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Lignocellulosic biomass, encompassing cellulose, lignin and hemicellulose in plant secondary cell walls (SCWs), is the most abundant source of renewable materials on earth. Currently, fast-growing woody dicots such as Eucalyptus and Populus trees are major lignocellulosic (wood fiber) feedstocks for bioproducts such as pulp, paper, cellulose, textiles, bioplastics and other biomaterials. Processing wood for these products entails separating the biomass into its three main components as efficiently as possible without compromising yield. Glucuronoxylan (xylan), the main hemicellulose present in the SCWs of hardwood trees carries chemical modifications that are associated with SCW composition and ultrastructure, and affect the recalcitrance of woody biomass to industrial processing. In this review we highlight the importance of xylan properties for industrial wood fiber processing and how gaining a greater understanding of xylan biosynthesis, specifically xylan modification, could yield novel biotechnology approaches to reduce recalcitrance or introduce novel processing traits. Altering xylan modification patterns has recently become a focus of plant SCW studies due to early findings that altered modification patterns can yield beneficial biomass processing traits. Additionally, it has been noted that plants with altered xylan composition display metabolic differences linked to changes in precursor usage. We explore the possibility of using systems biology and systems genetics approaches to gain insight into the coordination of SCW formation with other interdependent biological processes. Acetyl-CoA, s-adenosylmethionine and nucleotide sugars are precursors needed for xylan modification, however, the pathways which produce metabolic pools during different stages of fiber cell wall formation still have to be identified and their co-regulation during SCW formation elucidated. The crucial dependence on precursor metabolism provides an opportunity to alter xylan modification patterns through metabolic engineering of one or more of these interdependent pathways. The complexity of xylan biosynthesis and modification is currently a stumbling point, but it may provide new avenues for woody biomass engineering that are not possible for other biopolymers.

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Synthesis of xylan carbonates – An approach towards reactive polysaccharide derivatives showing self-assembling into nanoparticles

Cited by 23 publications

References 28 publications

Nanoparticles Based on Hydrophobic Polysaccharide Derivatives—Formation Principles, Characterization Techniques, and Biomedical Applications

Nanoparticles Based on Hydrophobic Polysaccharide Derivatives—Formation Principles, Characterization Techniques, and Biomedical Applications

Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates

Xylan in the Middle: Understanding Xylan Biosynthesis and Its Metabolic Dependencies Toward Improving Wood Fiber for Industrial Processing

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