Chemical synthesis of a dextran model, poly‐α‐(1 → 6)‐anhydro‐<scp>D</scp>‐glucopyranose

Ruckel, E. R.; Schuerch, Conrad

doi:10.1002/bip.1967.360050606

Cited by 68 publications

(13 citation statements)

References 16 publications

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“…It is a type of α-glucan produced from sucrose by the bacterial extracellular enzyme dextransucrase. Usually, it is synthesized by bacteria like Leuconostoc, Gluconobacter, Streptococcus and Lactobacillus [265][266][267][268][269][270][271][272][273]. Dextran is well soluble in water and several other organic solvents, such as methyl sulfoxide, formamide, ethylene glycol and glycerol.…”

Section: Neutral Polysaccharides: Dextransmentioning

confidence: 99%

Coating Matters: Review on Colloidal Stability of Nanoparticles with Biocompatible Coatings in Biological Media, Living Cells and Organisms

Schubert

Chanana

2018

CMC

108

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Within the last two decades, the field of nanomedicine has not developed as successfully as has widely been hoped for. The main reason for this is the immense complexity of the biological systems, including the physico-chemical properties of the biological fluids as well as the biochemistry and the physiology of living systems. The nanoparticles' physico-chemical properties are also highly important. These differ profoundly from those of freshly synthesized particles when applied in biological/living systems as recent research in this field reveals. The physico-chemical properties of nanoparticles are predefined by their structural and functional design (core and coating material) and are highly affected by their interaction with the environment (temperature, pH, salt, proteins, cells). Since the coating material is the first part of the particle to come in contact with the environment, it does not only provide biocompatibility, but also defines the behavior (e.g. colloidal stability) and the fate (degradation, excretion, accumulation) of nanoparticles in the living systems. Hence, the coating matters, when designing a nanoparticle system for biomedical applications, which has to fulfill its task in the complex environment of biological fluids, cells and organisms. In this review, we evaluate the performance of different coating materials for nanoparticles concerning their ability to provide colloidal stability in biological media and living systems.

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Section: Neutral Polysaccharides: Dextransmentioning

confidence: 99%

Coating Matters: Review on Colloidal Stability of Nanoparticles with Biocompatible Coatings in Biological Media, Living Cells and Organisms

Schubert

Chanana

2018

CMC

108

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“…As shown in Table 1, when the concentration of PF 5 was lower than 5 mol % relative to the monomer, a trace amount of polymer was obtained (entries 1 and 2). Increasing the concentration to 10 mol % PF 5 gave polymers with M n =15 500-19 600 in 8 to 22% yields (entries [3][4][5][6][7][8]. At 20 mol % PF 5 , the yield was slightly improved, but the M n of the polymers was decreased (entries 3 and 9, 4 and 10, 5 and 11, 6 and 12).…”

Section: Resultsmentioning

confidence: 94%

Ring-Opening Polymerization of a Benzylated 1,6-Anhydro-β-d-talopyranose and Synthesis of a New Polysaccharide, (1→6)-α-d-Talopyranan

Hattori

Yoshida

2009

Macromolecules

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1,6-Anhydro-2,3,4-tri-O-benzyl-β-D-talopyranose (1) was synthesized and polymerized to compare its polymerizability with that of other benzylated 1,6-anhydrohexopyranoses reported previously. In methylene chloride at -60°C, phosphorus pentafluoride as the initiator gave stereoregular polymers (2) with number-average molecular weights (M n ) of 9500-19 600. The polymerizability was analyzed based on the configuration of the hydroxyl groups and conformational change of the pyranose ring during polymerization. The monomer reactivity ratios resulting from copolymerization with 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (4) were also compared. The present monomer 1 required a large amount of the initiator for polymerization. 31 P NMR results of polymerization suggested that considerable amounts of the initiator coordinated with not only the oxygen of the 1,6-anhydro ring of the monomer but also those of the polymer. This additional coordination of the initiator with the polymer oxygens is expected to decrease the initiation efficiency. Debenzylation resulted in a new stereoregular polysaccharide, (1f6)-R-D-talopyranan (3).

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“…The polymerisation of 1,6-anhydro-2,3,4-tri-O-benzyl-β-d-glucopyranose with phosphorous pentafluoride as catalyst under high vacuum and subsequent cleavage of the benzyl ether linkage by Birch reduction leads to dextrans with M n 41 800-75 750 g mol -1 [84,86]. Furthermore, tri-O-methyl-glucopyranose and tri-O-ethyl-glucopyranose can serve as monomer but yield a low molecular weight or rather polydisperse polymer (Table 4).…”

Section: Chemical Synthesis Of Dextranmentioning

confidence: 99%

Functional Polymers Based on Dextran

Heinze

Liebert

Heublein

et al.

Advances in Polymer Science

248

198

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Dextran, comprising a family of neutral polysaccharides consisting of an α-(1→6) linked d-glucose main chain with varying proportions of linkages and branches, depending on the bacteria used, is an interesting starting material for chemical modification reactions for the design of new functional polymers with promising properties. The review summarises recent results on structure characterisation of dextran including some comments on biosynthesis of this important class of biopolymers. Applications of dextran are discussed as well. Chemical modification reactions of dextran are increasingly studied for the structure and hence property design. The review highlights recent progress in esterification of dextran, both inorganic and organic polysaccharide esters, etherification reactions towards ionic and non-ionic ethers, and the huge variety of different conversions mainly developed for the binding of drugs. It summarises recent developments in the application of dextran derivatives with a focus on the chemical structures behind these materials such as prodrugs, bioactivity of inorganic dextran esters, heparin sulfate mimics, hydrogels, nanoparticles and self assembly structures for surface modification. Keywords Functionalised dextran • Structural analysis • Prodrugs • Nanostructures • Bioactivity Abbreviations AFM Atomic force microscopy AGU Anhydroglucose units AT Antithrombin AZT Azidothymidine BSH Na 2 B 12 H 11 SH BSA Bovine serum albumin CAC Critical association concentration CDI N,N -Carbonyldiimidazole CMC Critical micelle concentration CMD Carboxymethyl dextran CMDB Carboxymethyl dextran benzylamide CMDBSSu Carboxymethyl dextran benzylamidesulfonate sulfate CMDBSu Carboxymethyl dextran benzylamide sulfate CMDEE Carboxymethyl dextran ethyl ester CMDSu Carboxymethyl dextran sulfate COSY Two-dimensional correlated spectroscopy CsA Cyclosporin A 2D Two-dimensional Dach-Pt cis-Dihydroxo(cyclohexane-trans-l-1,2-diamine)platinum II DCC N,N -Dicyclohexylcarbodiimide T. Heinze et al.

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Chemical synthesis of a dextran model, poly‐α‐(1 → 6)‐anhydro‐D‐glucopyranose

Cited by 68 publications

References 16 publications

Coating Matters: Review on Colloidal Stability of Nanoparticles with Biocompatible Coatings in Biological Media, Living Cells and Organisms

Coating Matters: Review on Colloidal Stability of Nanoparticles with Biocompatible Coatings in Biological Media, Living Cells and Organisms

Ring-Opening Polymerization of a Benzylated 1,6-Anhydro-β-d-talopyranose and Synthesis of a New Polysaccharide, (1→6)-α-d-Talopyranan

Functional Polymers Based on Dextran

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