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Polymers
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Structural Modification of Polysaccharides
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Structural Modification of Polysaccharides

A special issue of Polymers (ISSN 2073-4360). This special issue belongs to the section "Biobased and Biodegradable Polymers".

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 33709

Special Issue Editors

Dr. Emiliano Bedini

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Guest Editor
Department of Chemical Sciences, Università degli Studi di Napoli Federico II, Complesso Universitario Monte S. Angelo, via Cintia 4, I‐80126 Napoli, Italy
Interests: semi‐synthetic polysaccharides; sulfated polysaccharides; NMR of polysaccharides; protecting groups in polysaccharide chemistry
Dr. Serena Traboni

E-Mail
Co-Guest Editor
Department of Chemical Sciences, Università degli Studi di Napoli Federico II, Naples, Italy
Interests: regioselective functionalization of carbohydrates; solvent-free reactions; orthogonal protecting groups; one-pot protection of carbohydrates; saccharide building blocks; semi-synthetic polysaccharides; regioselective modification of polysaccharides
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Polysaccharides are extremely common and widespread in nature. They play crucial roles in a huge number of research areas: health, biopharma, food, cosmetics, chemicals,  bioplastics, biopackaging, biotechnology, building, fuels, etc. For these reasons, the research of new chemical, enzymatic, or chemo‐enzymatic methods for obtaining polysaccharide derivatives from natural sources with novel properties and applications is a hot topic that is rapidly evolving in organic, polymer, as well as in biological chemistry, in spite of the severe difficulties in modifying the structure of polysaccharides (their generally poor solubility in several solvents, the necessity to avoid harsh reaction conditions that might cleave the polysaccharide chain, and their heterogeneity and/or polydispersity that hampers a detailed structural characterization).

This Special Issue is devoted to the most recent research on these topics, covering all the aspects concerning the structural modification and application of polysaccharides.

Dr. Emiliano Bedini
Dr. Serena Traboni
Guest Editors

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Keywords

  • synthetic methods
  • enzymatic synthesis
  • semi‐synthesis
  • structural modification
  • structural characterization
  • biomaterials
  • biopharmaceuticals
  • drug delivery
  • bioplastics
  • biopackaging

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Published Papers (7 papers)

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Research

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16 pages, 3546 KiB  
Article
Comprehensive Leaf Cell Wall Analysis Using Carbohydrate Microarrays Reveals Polysaccharide-Level Variation between Vitis Species with Differing Resistance to Downy Mildew
by Yu Gao, Xiangjing Yin, Haoyu Jiang, Jeanett Hansen, Bodil Jørgensen, John P. Moore, Peining Fu, Wei Wu, Bohan Yang, Wenxiu Ye, Shiren Song and Jiang Lu
Polymers 2021, 13(9), 1379; https://doi.org/10.3390/polym13091379 - 23 Apr 2021
Cited by 2 | Viewed by 3063
Abstract
The cell wall acts as one of the first barriers of the plant against various biotic stressors. Previous studies have shown that alterations in wall polysaccharides may influence crop disease resistance. In the grapevine family, several native species (e.g., Chinese wild grapevine) show [...] Read more.
The cell wall acts as one of the first barriers of the plant against various biotic stressors. Previous studies have shown that alterations in wall polysaccharides may influence crop disease resistance. In the grapevine family, several native species (e.g., Chinese wild grapevine) show a naturally higher resistance to microbial pathogens than cultivated species (e.g., Vitis vinifera), and this trait could be inherited through breeding. Despite the importance of the cell wall in plant immunity, there are currently no comprehensive cell wall profiles of grapevine leaves displaying differing resistance phenotypes, due to the complex nature of the cell wall and the limitations of analytical techniques available. In this study, the cutting-edge comprehensive carbohydrate microarray technology was applied to profile uninfected leaves of the susceptible cultivar (Vitis vinifera cv. “Cabernet Sauvignon”), a resistant cultivar (Vitis amurensis cv. “Shuanghong”) and a hybrid offspring cross displaying moderate resistance. The microarray approach uses monoclonal antibodies, which recognize polysaccharides epitopes, and found that epitope abundances of highly esterified homogalacturonan (HG), xyloglucan (with XXXG motif), (galacto)(gluco)mannan and arabinogalactan protein (AGP) appeared to be positively correlated with the high resistance of Vitis amurensis cv. “Shuanghong” to mildew. The quantification work by gas chromatography did not reveal any significant differences for the monosaccharide constituents, suggesting that polysaccharide structural alterations may contribute more crucially to the resistance observed; this is again supported by the contact infrared spectroscopy of cell wall residues, revealing chemical functional group changes (e.g., esterification of pectin). The identification of certain wall polysaccharides that showed alterations could be further correlated with resistance to mildew. Data from the use of the hybrid material in this study have preliminarily suggested that these traits could be inherited and may be applied as potential structural biomarkers in future breeding work. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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12 pages, 3286 KiB  
Article
Effect of Monochloroacetic Acid on Properties of Carboxymethyl Bacterial Cellulose Powder and Film from Nata de Coco
by Pornchai Rachtanapun, Warinporn Klunklin, Pensak Jantrawut, Noppol Leksawasdi, Kittisak Jantanasakulwong, Yuthana Phimolsiripol, Phisit Seesuriyachan, Thanongsak Chaiyaso, Warintorn Ruksiriwanich, Suphat Phongthai, Sarana Rose Sommano, Winita Punyodom, Alissara Reungsang and Thi Minh Phuong Ngo
Polymers 2021, 13(4), 488; https://doi.org/10.3390/polym13040488 - 4 Feb 2021
Cited by 23 | Viewed by 5019
Abstract
Nata de coco has been used as a raw material for food preparation. In this study, the production of carboxymethyl cellulose (CMC) film from nata de coco and the effect of monochloroacetic acid on carboxymethyl bacterial cellulose (CMCn) and its film [...] Read more.
Nata de coco has been used as a raw material for food preparation. In this study, the production of carboxymethyl cellulose (CMC) film from nata de coco and the effect of monochloroacetic acid on carboxymethyl bacterial cellulose (CMCn) and its film were investigated. Bacterial cellulose from nata de coco was modified into CMC form via carboxymethylation using various concentrations of monochloroacetic acid (MCA) at 6, 12, 18, and 24 g per 15 g of cellulose. The results showed that different concentrations of MCA affected the degree of substitution (DS), chemical structure, viscosity, color, crystallinity, and morphology of CMCn. The optimum treatment for carboxymethylation was found using 24 g of MCA per 15 g of cellulose, which provided the highest DS at 0.83. The morphology of CMCn was related to DS value; a higher DS value showed denser and smoother surface than nata de coco cellulose. The various MCA concentrations increased the mechanical properties (tensile strength and percentage of elongation at break) and water vapor permeability of CMCn, which were related to the DS value. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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16 pages, 3572 KiB  
Article
Deciphering Structural Determinants in Chondroitin Sulfate Binding to FGF-2: Paving the Way to Enhanced Predictability of Their Biological Functions
by Giulia Vessella, José Antonio Vázquez, Jesús Valcárcel, Laura Lagartera, Dianélis T. Monterrey, Agatha Bastida, Eduardo García-Junceda, Emiliano Bedini, Alfonso Fernández-Mayoralas and Julia Revuelta
Polymers 2021, 13(2), 313; https://doi.org/10.3390/polym13020313 - 19 Jan 2021
Cited by 14 | Viewed by 4685
Abstract
Controlling chondroitin sulfates (CSs) biological functions to exploit their interesting potential biomedical applications requires a comprehensive understanding of how the specific sulfate distribution along the polysaccharide backbone can impact in their biological activities, a still challenging issue. To this aim, herein, we have [...] Read more.
Controlling chondroitin sulfates (CSs) biological functions to exploit their interesting potential biomedical applications requires a comprehensive understanding of how the specific sulfate distribution along the polysaccharide backbone can impact in their biological activities, a still challenging issue. To this aim, herein, we have applied an “holistic approach” recently developed by us to look globally how a specific sulfate distribution within CS disaccharide epitopes can direct the binding of these polysaccharides to growth factors. To do this, we have analyzed several polysaccharides of marine origin and semi-synthetic polysaccharides, the latter to isolate the structure-activity relationships of their rare, and even unnatural, sulfated disaccharide epitopes. SPR studies revealed that all the tested polysaccharides bind to FGF-2 (with exception of CS-8, CS-12 and CS-13) according to a model in which the CSs first form a weak complex with the protein, which is followed by maturation to tight binding with kD ranging affinities from ~1.31 μM to 130 μM for the first step and from ~3.88 μM to 1.8 nM for the second one. These binding capacities are, interestingly, related with the surface charge of the 3D-structure that is modulated by the particular sulfate distribution within the disaccharide repeating-units. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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14 pages, 4345 KiB  
Article
Chemical Modification of Pullulan Exopolysaccharide by Grafting Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBHV) via Click Chemistry
by Layde T. de Carvalho, Maria Luiza da S. Paula, Rodolfo M. de Moraes, Gizelda M. Alves, Talita M. Lacerda, Julio C. dos Santos, Amilton M. dos Santos and Simone de F. Medeiros
Polymers 2020, 12(11), 2527; https://doi.org/10.3390/polym12112527 - 29 Oct 2020
Cited by 9 | Viewed by 3276
Abstract
Biodegradable and biocompatible copolymers have been often studied for the development of biomaterials for drug delivery systems. In this context, this work reports the synthesis and characterization of a novel pullulan-g-poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (Pull-g-PHBHV) graft copolymer using click chemistry. [...] Read more.
Biodegradable and biocompatible copolymers have been often studied for the development of biomaterials for drug delivery systems. In this context, this work reports the synthesis and characterization of a novel pullulan-g-poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (Pull-g-PHBHV) graft copolymer using click chemistry. Well-defined and functional pullulan backbones containing azide groups (PullN3) previously prepared by our group were successfully used for this purpose and propargyl-terminated poly(3-hydroxybutyrate-co-3-hydroxyvalerate) was prepared via transesterification using propargyl alcohol as a chain transfer agent. By an alkyne-azide cycloaddition reaction catalyzed by copper (Cu (I)) (CuAAC), the graft copolymer Pull-g-PHBHV was obtained. The chemical structures of the polymers were accessed by 1H NMR and 13C NMR FTIR. Disappearance of the bands referring to the main bonds evidenced success in the grafting reaction. Besides that, DRX, DSC and TGA were used in order to access the changes in crystallinity and thermal behavior of the material. The remaining crystallinity of the Pull-g-PHBHV structure evidences the presence of PHBHV. Pull-g-PHBHV presented lower degradation maximum temperature values than the starting materials, indicating its minor thermal stability. Finally, the synthesized material is an innovative biopolymer, which has never been reported in the previous literature. It is a bio-derived and biodegradable polymer, chemically modified, resulting in interesting properties which can be useful for their further applications as biomedical systems for controlled delivery, for example. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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15 pages, 3100 KiB  
Article
Kappa-Carrageenan-Based Dual Crosslinkable Bioink for Extrusion Type Bioprinting
by Wonseop Lim, Gyeong Jin Kim, Hyun Woo Kim, Jiyeon Lee, Xiaowei Zhang, Min Gyeong Kang, Jeong Wook Seo, Jae Min Cha, Hyun Jin Park, Min-Young Lee, Su Ryon Shin, Seon Young Shin and Hojae Bae
Polymers 2020, 12(10), 2377; https://doi.org/10.3390/polym12102377 - 15 Oct 2020
Cited by 54 | Viewed by 5690
Abstract
Bioink based 3D bioprinting is a promising new technology that enables fabrication of complex tissue structures with living cells. The printability of the bioink depends on the physical properties such as viscosity. However, the high viscosity bioink puts shear stress on the cells [...] Read more.
Bioink based 3D bioprinting is a promising new technology that enables fabrication of complex tissue structures with living cells. The printability of the bioink depends on the physical properties such as viscosity. However, the high viscosity bioink puts shear stress on the cells and low viscosity bioink cannot maintain complex tissue structure firmly after the printing. In this work, we applied dual crosslinkable bioink using Kappa-carrageenan (κ-CA) to overcome existing shortcomings. κ-CA has properties such as biocompatibility, biodegradability, shear-thinning and ionic gelation but the difficulty of controlling gelation properties makes it unsuitable for application in 3D bioprinting. This problem was solved by synthesizing methacrylated Kappa-carrageenan (MA-κ-CA), which can be dual crosslinked through ionic and UV (Ultraviolet) crosslinking to form hydrogel using NIH-3T3 cells. Through MA substitutions, the rheological properties of the gel could be controlled to reduce the shear stress. Moreover, bioprinting using the cell-laden MA-κ-CA showed cell compatibility with enhanced shape retention capability. The potential to control the physical properties through dual crosslinking of MA-κ-CA hydrogel is expected to be widely applied in 3D bioprinting applications. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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13 pages, 3287 KiB  
Article
Structural Characterization of Glycerophosphorylated and Succinylated Cyclic β-(1→2)-d-Glucan Produced by Sinorhizobium mliloti 1021
by Hyojeong Lee, Seonmok Kim, Yohan Kim and Seunho Jung
Polymers 2020, 12(9), 2073; https://doi.org/10.3390/polym12092073 - 12 Sep 2020
Cited by 5 | Viewed by 2422
Abstract
Rhizobia produces different types of surface polysaccharides. Among them, cyclic β-(1→2)-d-glucan is located in the periplasmic space of rhizobia and plays an important role in the adaptation of bacteria to osmotic adaptation. Cyclic β-(1→2)-d-glucan (CG), synthesized from Sinorhiozbbium meliloti [...] Read more.
Rhizobia produces different types of surface polysaccharides. Among them, cyclic β-(1→2)-d-glucan is located in the periplasmic space of rhizobia and plays an important role in the adaptation of bacteria to osmotic adaptation. Cyclic β-(1→2)-d-glucan (CG), synthesized from Sinorhiozbbium meliloti 1021, has a neutral and anionic form. In the present study, we characterized the exact chemical structures of anionic CG after purification using size exclusion s (Bio-Gel P-6 and P-2) chromatography, and DEAE-Sephadex anion exchange chromatography. The exact structure of each isolated anionic CG was characterized using various analytical methods such as nuclear magnetic resonance (NMR), attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopy and matrix associated laser desorption ionization-time of Flight (MALDI-TOF) mass spectrometry. The precise chemical structures of novel anionic CG molecules were elucidated by various NMR spectroscopic analyses, including 1H, 13C, 31P, and 2D HSQC NMR spectroscopy. As a result, we discovered that anionic CG molecules have either glycerophosphoryl or succinyl residues at C6 positions of a neutral CG. In addition, the results of MALDI-TOF mass spectrometric analysis confirmed that there are two types of patterns for anionic CG peaks, where one type of peak was the succinylated CG (SCG) and the other was glycerophospholated CG (GCG). In addition, it was revealed that each anionic CG has one to four substituents of the succinyl group of SCG and glycerophosphoryl group of GCG, respectively. Anionic CG could have potential as a cyclic polysaccharide for drug delivery systems and a chiral separator based on the complexation with basic target molecules. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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Review

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41 pages, 3123 KiB  
Review
An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
by Emanuelle Dantas Freitas, Celso Fidelis Moura Jr., Jonas Kerwald and Marisa Masumi Beppu
Polymers 2020, 12(12), 2878; https://doi.org/10.3390/polym12122878 - 30 Nov 2020
Cited by 83 | Viewed by 8516
Abstract
Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its solubility over a [...] Read more.
Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its solubility over a wide pH range and, consequently, expand its range of applications. Quaternization occurs by introducing a quaternary ammonium moiety onto or outside the chitosan backbone, via chemical reactions with primary amino and hydroxyl groups, under vast experimental conditions. The oldest and most common forms of quaternized chitosan involve N,N,N-trimethyl chitosan (TMC) and N-[(2-hydroxy-3-trimethyl ammonium) propyl] chitosan (HTCC) and, more recently, quaternized chitosan by insertion of pyridinium or phosphonium salts. By modifying chitosan through the insertion of a quaternary moiety, permanent cationic charges on the polysaccharide backbone are achieved and properties such as water solubility, antimicrobial activity, mucoadhesiveness and permeability are significantly improved, enabling the application mainly in the biomedical and pharmaceutical areas. In this review, the main quaternized chitosan compounds are addressed in terms of their structure, properties, synthesis routes and applications. In addition, other less explored compounds are also presented, involving the main findings and future prospects regarding the field of quaternized chitosans. Full article
(This article belongs to the Special Issue Structural Modification of Polysaccharides)
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