Synthesis and Structure/Property Relationships of Regioselective 2‐O‐, 3‐O‐ and 6‐O‐Ethyl Celluloses

Kamitakahara, Hiroshi; Funakoshi, Toshihiro; Nakai, Shunji; Takano, Toshiyuki; Nakatsubo, Fumiaki

doi:10.1002/mabi.200900392

Cited by 9 publications

(4 citation statements)

References 16 publications

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“…As well as the degree of substitution, the distribution of functional groups strongly influences the properties of polysaccharide derivatives. , By controlling the sites at which substituents are attached to curdlan, researchers can modify its physical properties, such as solubility, crystallinity and thermal characteristics of the obtained regioselectively substituted derivatives, permitting detailed study of structure–property relationships. Regioselectively modified curdlan derivatives have many potential applications including as food additives, in drug and gene delivery, and as antitumor, anti-infective, or anti-inflammatory agents .…”

Section: Curdlan Derivatizationmentioning

confidence: 99%

Properties, Chemistry, and Applications of the Bioactive Polysaccharide Curdlan

2014

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Curdlan is a bacterial polysaccharide that has been of significant recent interest due to its interesting and valuable rheological properties and its inherent bioactivity. The simple (1→3)-β-glucan homopolymeric, unbranched structure of curdlan is conducive to enhanced solubility relative to many other abundant natural polysaccharides, thus, providing alternatives for processing the polymer into desired shapes and formulations. At the same time, this relatively good solubility enables chemical modification under mild conditions, leading to a growing body of literature on derivative chemistry, structure-property relationships, and the potential for regioselective modification. Structure, properties, biosynthesis, modification chemistries, and key applications are the foci for this review of the curdlan literature.

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Section: Curdlan Derivatizationmentioning

confidence: 99%

Properties, Chemistry, and Applications of the Bioactive Polysaccharide Curdlan

2014

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“…These syntheses of the different methylcelluloses are elegant and useful; they have already permitted NMR studies of the individual regiospecifically substituted homopolymers, characterization of film properties, and the utilization of these homopolymers as blocks in subsequent syntheses of blocky cellulose ether derivatives, − just to name a few representative studies. Kamitakahara, Nakatsubo, and Rosenau have demonstrated that these methods are rather general for cellulose ethers; indeed, their only drawbacks for the synthesis of regiospecifically substituted cellulose ethers appear to be their multistep nature and the fact that the attainable DP of the products is limited (depending at least in part on the types of 3,6-substituents on the glucose-1,2,4-orthopivalate monomer; 3,6-di- O -benzyl monomer gives DP approaching 20, mixed 3,6- O -(pivalate ester/benzyl ether) derivatives give DPs in the 5–10 range, and some simple 3,6-dialkyl ether monomers have afforded alkylcelluloses of DP 20–70). An example of the interesting structure–property studies enabled by these synthetic methods is the synthesis of regiospecifically substituted cellulose ethers containing methyl and ethyl substituents; the impact of regiochemistry on solubility is highlighted in Table , adapted from the Kamitakahara article …”

Section: De Novo Synthesis Of Cellulose Derivativesmentioning

confidence: 99%

Regioselective Esterification and Etherification of Cellulose: A Review

et al. 2011

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Deep understanding of the structure-property relationships of polysaccharide derivatives depends on the ability to control the position of the substituents around the monosaccharide ring and along the chain. Equally important is the ability to analyze position of substitution. Historically, both synthetic control and analysis of regiochemistry have been very difficult for cellulose derivatives, as for most other polysaccharide derivatives. With the advent of cellulose solvents that are suitable for chemical transformations, it has become possible to carry out cellulose derivatization under conditions sufficiently mild to permit increasingly complete regiochemical control, particularly with regard to the position of the substituents around the anhydroglucose ring. In addition, new techniques for forming cellulose and its derivatives from monomers, either by enzyme-catalyzed processes or chemical polymerization, permit us to address new frontiers in regiochemical control. We review these exciting developments in regiocontrolled synthesis of cellulose derivatives and their implications for in-depth structure-property studies.

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“…Commercial HPC (MS 3.0–4.0) is soluble in water below 38 °C, but has the interesting thermal gelation property in common with MC and some other cellulose ethers . As a result of this thermal gelation, HPC is insoluble in water above about 45 °C.…”

Section: Common Types Of Cellulose Ethers; Syntheses Properties and A...mentioning

confidence: 99%

“…Commercial HPC (MS 3.0−4.0) 173 is soluble in water below 38 °C, but has the interesting thermal gelation property in common with MC 121 and some other cellulose ethers. 174 As a result of this thermal gelation, HPC is insoluble in water above about 45 °C. HPC is available in a range of molecular weights, which influence solution properties in predictable ways.…”

Section: Nacmc Synthesis and General Polymer Propertiesmentioning

confidence: 99%

Pharmaceutical Applications of Cellulose Ethers and Cellulose Ether Esters

Arca¹,

et al. 2018

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Cellulose ethers have proven to be highly useful natural-based polymers, finding application in areas including food, personal care products, oil field chemicals, construction, paper, adhesives, and textiles. They have particular value in pharmaceutical applications due to characteristics including high glass transition temperatures, high chemical and photochemical stability, solubility, limited crystallinity, hydrogen bonding capability, and low toxicity. With regard to toxicity, cellulose ethers have essentially no ability to permeate through gastrointestinal enterocytes and many are already in formulations approved by the U.S. Food and Drug Administration. We review pharmaceutical applications of these valuable polymers from a structure-property-function perspective, discussing each important commercial cellulose ether class; carboxymethyl cellulose, methyl cellulose, hydroxypropylcellulose, hydroxypropyl methyl cellulose, and ethyl cellulose, and cellulose ether esters including hydroxypropyl methyl cellulose acetate succinate and carboxymethyl cellulose acetate butyrate. We also summarize their syntheses, basic material properties, and key pharmaceutical applications.

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Synthesis and Structure/Property Relationships of Regioselective 2‐O‐, 3‐O‐ and 6‐O‐Ethyl Celluloses

Cited by 9 publications

References 16 publications

Properties, Chemistry, and Applications of the Bioactive Polysaccharide Curdlan

Properties, Chemistry, and Applications of the Bioactive Polysaccharide Curdlan

Regioselective Esterification and Etherification of Cellulose: A Review

Pharmaceutical Applications of Cellulose Ethers and Cellulose Ether Esters

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