Towards unnatural xylan based polysaccharides: reductive amination as a tool to access highly engineered carbohydrates

Daus, Stephan; Elschner, Thomas; Heinze, Thomas

doi:10.1007/s10570-010-9421-y

Cited by 28 publications

(15 citation statements)

References 20 publications

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“…Amination of different polysaccharides also has been reported. A xylan with small molecular weight was modified at the reducing end by reductive amination, causing an increased molecular weight of the coupling products in comparison with the original material (Dausand others ).…”

Section: The Effect Of Molecular Modification On Physical and Chemicamentioning

confidence: 99%

Molecular Modification of Polysaccharides and Resulting Bioactivities

Xiong

Lai

et al. 2015

Comp Rev Food Sci Food Safe

415

172

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Polysaccharides are ideal natural resources for supplements and pharmaceuticals that have received more and more attention over the years. Natural polysaccharides have been shown to have fewer side effects, but because of their inherently physicochemical properties, their bioactivities were difficult to compare with those of synthetic drugs. Thus, researchers have modified the structures and properties of natural polysaccharides based on structure-activity relationships and have obtained better functionally improved polysaccharides. This review focuses on the major modification methods of polysaccharides, and discusses the effect of molecular modification on their physicochemical properties and bioactivities. Molecular modification methods mainly include chemical, physical, and biological changes. Chemical modification is the most widely used method; it can significantly increase the water solubility and bioactivities of polysaccharides by grafting onto other groups. Physical and biological modifications only change the molecular weight of a polysaccharide, and thereby change its physicochemical properties and bioactivities. Most of the molecular modifications bring about an increase in the antioxidant activity of polysaccharides, and among these, sulfated and acetylated modifications are very common. Furthermore, phosphorylation modification is the most common application to increase antitumor activity, and modified polysaccharides have been shown to have anti-HIV activity as the result of sulfated modification.

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Section: The Effect Of Molecular Modification On Physical and Chemicamentioning

confidence: 99%

Molecular Modification of Polysaccharides and Resulting Bioactivities

Xiong

Lai

et al. 2015

Comp Rev Food Sci Food Safe

415

172

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“…Cellulose, dextran, and other polysaccharides like alginates, chitosans, hyaluronan, scleroglucan, and schizophyllane may be converted with sodium periodate to cleave glycol structure yielding dialdehyde moieties. In the next step, a Schiff base is formed by addition of an amine, which may be reduced with sodium borohydride, sodium cyanoborohydride, or sodium triacetoxyborohydride . This method is often used for coupling of polysaccharides, e.g., dextran, with enzymes and proteins .…”

Section: Activation Of Polysaccharidesmentioning

confidence: 99%

Cellulose Carbonates: A Platform for Promising Biopolymer Derivatives With Multifunctional Capabilities

Elschner

Heinze

2015

Macromolecular Bioscience

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Cellulose carbonates as a platform compound open new possibilities for the design of advanced materials based on the most important renewable resource cellulose. In the present feature, the chemistry of cellulose carbonates is discussed considering own research results adequately. After a short overview about methods for activation of polysaccharides for a conversion with nucleophilic compounds in particular with amines, details about various methods for the synthesis of polysaccharide carbonates are discussed. The main issue of the feature is the synthesis and aminolysis of cellulose carbonates with low, intermediate, and high degree of substitution and the evaluation of this chemistry with respect to specific challenges. Functional cellulose carbamates, obtained from cellulose phenyl carbonate by aminolysis, show the potential use of this class of celluloses. Immunoassays and zwitterionic polymers are included as representative examples regarding properties and application of the new cellulose-based products.

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“…Using renewable materials, more eco-friendliness can be achieved relative to the conventional toxic synthetic polymer composites materials [10][11][12]. But the strong inter-and intra-molecular hydrogen bonding between the hydroxyl groups in the glucopyranose units, the nature homopolymer has not only higher degree of polymerization (DP) but also higher crystallization, which is not favorable for reagents accessing to the hydroxyl groups [13]. Cellulose therefore has limited modification.…”

Section: Introductionmentioning

confidence: 99%