Chemospecific manipulations of a rigid polysaccharide: syntheses of novel chitosan derivatives with excellent solubility in common organic solvents by regioselective chemical modifications

Nishimura, Shin‐Ichiro; Kohgo, Osamu; Kurita, Keisuke; Kuzuhara, Hiroyoshi

doi:10.1021/ma00017a003

Cited by 299 publications

(192 citation statements)

References 5 publications

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“…Among these diverse applications, chitosan has a great role in food industry and agriculture (Chien et al, 2007a;. Much attention has been paid currently to chitosan as a potential polysaccharide resource (Nishimura et al, 1991). Several efforts have been carried out to prepare r.a. Shiekh et al (Rinaudo et al, 1999a;Rinaudo et al, 1999b).…”

Section: Introductionmentioning

confidence: 99%

Chitosan as a Novel Edible Coating for Fresh Fruits

Shiekh

Malik

Al-Thabaiti

et al. 2013

FSTR

125

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Section: Introductionmentioning

confidence: 99%

Chitosan as a Novel Edible Coating for Fresh Fruits

Shiekh

Malik

Al-Thabaiti

et al. 2013

FSTR

125

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“…The precipitate was filtered, washed with methanol overnight, and vacuum dried. 18,21 synthesis of Pegylated chitosan (chitosan-O-Peg)…”

Section: Phthaloylation Of Chitosanmentioning

confidence: 99%

“…17 This study aims to achieve facile chemoselective conjugation of PEG at the hydroxyl group of chitosan, where the amine groups of chitosan were first protected using phthalic anhydride. 18 Nanoparticles were formed using an ionic gelation method. The concentration of the polymer versus crosslinker and the pH of the solution were adjusted with reference to our previously optimized study.…”

Section: Introductionmentioning

confidence: 99%

A novel method for synthesizing PEGylated chitosan nanoparticles: strategy, preparation, and in vitro analysis

Malhotra

Lane²,

Tomaro-Duchesneau

et al. 2011

IJN

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Preparation of poly (ethylene glycol) (PEG)-grafted chitosan is essential for improving the biocompatibility and water solubility of chitosan. Presently available methods for this have limitations. This article describes a new method for preparing PEGylated chitosan nanoparticles. For this chitosan was chemoselectively modified using a novel scheme at the C6 position of its repeating units by PEG. The amine groups at the C2 position of the chitosan were protected using phthalic anhydride. Sodium hydride was used to catalyze the etherification reaction between chlorinated chitosan and methyl-PEG, and PEG-grafted chitosan was successfully synthesized. Each step was characterized using 13 C nuclear magnetic resonance and Fourier transform infrared. After PEGylation the phthaloylated chitosan was successfully deprotected using hydrazine monohydrate. The synthetic scheme proposed demonstrates a new method for grafting PEG onto chitosan with a moderate degree of substitution. The potential of this polymer in nanoparticle preparation using an ionic gelation method and its gene delivery potentials were investigated by complexing a fluorescently labeled control siRNA. The result showed that suitable nanoparticles can be synthesized using this polymer and that they have capacity to carry genes and provide adequate transfection efficacy with no toxicity when tested in neuronal cells.

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“…Chitosan, which is deacetylated chitin [2], is a β-1,4-linked polymer of glucosamine (GlcN) that is soluble in dilute acids and viscous [3] and is widely used in textile goods, cosmetics, as food additives, and in medical applications [4] [5] [6] because of its antibacterial effects, biodegradability, and biocompatibility [7] [8].…”

Section: Introductionmentioning

confidence: 99%

Molecular Cloning and Phylogenetic Analysis of a Chitin Deacetylase Isolated from the Epidermis of the Red Snow Crab <i>Chionoecetes japonicas</i>

Fujimori¹,

Fukushima²,

Matsumiya³

2018

ABB

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Chitin deacetylase (CDA; EC 3. 5. 1. 41) catalyzes the deacetylation of chitin. In this study, we successfully cloned and sequenced a chitin deacetylase gene from the red snow crab Chionoecetes japonicus. By using reverse transcription-polymerase chain reaction (RT-PCR) and 5' and 3' rapid amplification of cDNA ends, we obtained a 2141-bp amplicon containing a chitin deacetylase gene (CjCDA) from the epidermis of C. japonicus. The amplicon contains a 1575-bp open reading frame that is predicted to encode a 525-amino acid protein. The structure predicted from the deduced amino acid sequence included an N-terminal signal peptide, chitin-binding domain (CBD), low-density lipoprotein receptor class A domain (LDL-A), and catalytic domain. Comparative analysis of the deduced amino acid sequence of CjCDA revealed the highest homology (74%) to gastrolith protein 59 of Cherax quadricarinatus. We used RT-PCR to evaluate the expression of CjCDA in various tissues of C. japonicus, and we observed that CjCDA was expressed only in the epidermis. A phylogenetic analysis, using the amino acid sequences of CjCDA and other known chitin deacetylases, showed that CjCDA belonged to a group of crustacean chitin deacetylases. To our knowledge, this is the first study reporting the cDNA cloning of a chitin deacetylase from a crab.

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Chemospecific manipulations of a rigid polysaccharide: syntheses of novel chitosan derivatives with excellent solubility in common organic solvents by regioselective chemical modifications

Cited by 299 publications

References 5 publications

Chitosan as a Novel Edible Coating for Fresh Fruits

Chitosan as a Novel Edible Coating for Fresh Fruits

A novel method for synthesizing PEGylated chitosan nanoparticles: strategy, preparation, and in vitro analysis

Molecular Cloning and Phylogenetic Analysis of a Chitin Deacetylase Isolated from the Epidermis of the Red Snow Crab <i>Chionoecetes japonicas</i>

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Chemospecific manipulations of a rigid polysaccharide: syntheses of novel chitosan derivatives with excellent solubility in common organic solvents by regioselective chemical modifications

Cited by 299 publications

References 5 publications

Chitosan as a Novel Edible Coating for Fresh Fruits

Chitosan as a Novel Edible Coating for Fresh Fruits

A novel method for synthesizing PEGylated chitosan nanoparticles: strategy, preparation, and in vitro analysis

Molecular Cloning and Phylogenetic Analysis of a Chitin Deacetylase Isolated from the Epidermis of the Red Snow Crab &lt;i&gt;Chionoecetes japonicas&lt;/i&gt;

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Molecular Cloning and Phylogenetic Analysis of a Chitin Deacetylase Isolated from the Epidermis of the Red Snow Crab <i>Chionoecetes japonicas</i>