Chemical Modification of Chitosan. 13. Synthesis of Organosoluble, Palladium Adsorbable, and Biodegradable Chitosan Derivatives toward the Chemical Plating on Plastics

Sashiwa, Hitoshi; Kawasaki, Norioki; Nakayama, Atsuyoshi; Muraki, Einosuke; Yamamoto, Noboru; Zhu, Hong; Nagano, Hiroshi; Omura, Yoshihiko; Saimoto, Hiroyuki; Shigemasa, Yoshihiro; Aiba, Sei‐ichi

doi:10.1021/bm0200478

Cited by 71 publications

(49 citation statements)

References 11 publications

(15 reference statements)

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“…[14] Detailed structural information about the SCC complex was obtained by 1 H NMR analysis [ Figure 2(B)]. [15,16] The sulfate/amino group ratio in the complexes was calculated according to the integrated area ratio between the peaks at 0.85 ppm (CH 3 in SDS) and 2.85 ppm (H2 of unsubstituted glucosamine in chitosan). Varying the SDS/chitosan feed ratio could modulate the sulfate/amino groups ratio in the complexes (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…The presence of PEG in the copolymers was confirmed by the appearance of a peak at 3. reaction was carried out. The remaining amino groups in SCC-g-PEG were calculated according to the integration area ratios between the peaks of NHAc at 1.85 ppm and H-2 of the GlcN residue at 2.85 ppm, [15] assuming that the deacetylation degree of chitosan remained unchanged after the conjugation reaction due to the very mild reaction conditions. The assignment of the peak at 2.85 ppm to the H-2 of the unsubstituted glucosamine residue in chitosan has been frequently reported previously.…”

Section: Synthesis Of Scc-g-pegmentioning

confidence: 99%

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A Facile Route for Regioselective Conjugation of Organo‐Soluble Polymers onto Chitosan

Cai

Jiang

et al. 2009

Macromolecular Bioscience

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A facile route is described for the regioselective conjugation of organo-soluble polymers onto chitosan under very mild conditions, using SCC as intermediates. SCC could be prepared simply by mixing chitosan acidic aqueous solution with SDS. PEG or PCL were then grafted to SCC using the NHS/DCC coupling method. In addition, the polymers were found to be linked to chitosan through the hydroxyl groups of chitosan when stoichiometric SCC was used as a precursor. SDS could be removed simply by either precipitating the solution of SCC-graft-polymer in DMSO into Tris aqueous solution or dialyzing against Tris solution.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Scc-g-pegmentioning

confidence: 99%

A Facile Route for Regioselective Conjugation of Organo‐Soluble Polymers onto Chitosan

Cai

Jiang

et al. 2009

Macromolecular Bioscience

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“…Another advantage of chitosan, which makes it highly desirable, is the capability of being chemically modified [8]. Through chemical modification, a great deal of chitosan derivatives have been prepared to promote their biological activity [9][10][11][12][13]. However, the application of chitosan is restricted to only acidic conditions where the NH 2 group becomes protonated [14,15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

Tan

Zhang

et al. 2016

International Journal of Biological Macromolecules

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a b s t r a c tChitosan is an abundant and renewable polysaccharide, which exhibits attractive bioactivities and natural properties. Improvement such as chemical modification of chitosan is often performed prior to further utilization. Three novel water soluble chitosan derivatives containing 1,2,3-triazole with or without halogen was designed and synthesized. Their antifungal activity against three kinds of phytopathogens was estimated by hyphal measurement in vitro. The inhibitory property and water solubility of the synthesized chitosan derivatives exhibited a remarkable improvement over chitosan. It is hypothesized that thiazolyl groups enable the synthesized chitosan to possess obviously better antifungal activity. Moreover, CTCTS and BTCTS, which have halogens at the periphery of polymers, inhibited the growth of tested phytopathogens more effectively with inhibitory indices of 81-93% at 1.0 mg/mL. The halogens could have a synergistic effect with triazole as they exhibited antifungal activity and electron-withdrawing capacity, which improve the antifungal activity of chitosan derivatives.

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“…[1][2][3][4][5][6] To promote its antifungal activity, a large number of chitosan derivatives have been prepared such as N,O-(acyl)chitosan, hydroxyethylacryl chitosan, and acyl thiourea chitosan by performing chemical modification. [7][8][9][10][11] However, the application of chitosan and many chitosan derivatives is limited due to their solubility mostly in diluted organic solutions such as formic, acetic, and succinic acid, as well as in a very few inorganic solvents, such as hydrochloric, phosphoric, and nitric acid at pH below 6.5. 12 Therefore, it is strongly desired that chitosan derivatives with high antifungal ability and good water solubility are developed.…”

Section: Introductionmentioning

confidence: 99%

Novel triazolyl-functionalized chitosan derivatives with different chain lengths of aliphatic alcohol substituent: Design, synthesis, and antifungal activity

Tan

Zhang

et al. 2015

Carbohydrate Research

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A B S T R A C TChemical modification of chitosan is increasingly studied for its potential of providing new application for chitosan. Here, we modify chitosan at its primary hydroxyl via 'click chemistry', and a group of novel water soluble chitosan derivatives with substituted 1,2,3-triazolyl group were designed and synthesized. Aliphatic alcohols with different lengths were used as functional dendrons to improve the antifungal activity of chitosan derivatives. Meanwhile, their antifungal activity against two kinds of phytopathogens was estimated by hypha measurement in vitro. All the chitosan derivatives exhibited excellent activity against tested fungi. It is found that the antifungal activity of chitosan derivatives against the tested fungi increases with augment in the chain length of straight aliphatic alcohols. And the hydrophobic moiety (alkyl) at the periphery of the synthesized chitosan derivatives tends to affect their antifungal activity.

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Chemical Modification of Chitosan. 13. Synthesis of Organosoluble, Palladium Adsorbable, and Biodegradable Chitosan Derivatives toward the Chemical Plating on Plastics

Cited by 71 publications

References 11 publications

A Facile Route for Regioselective Conjugation of Organo‐Soluble Polymers onto Chitosan

A Facile Route for Regioselective Conjugation of Organo‐Soluble Polymers onto Chitosan

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

Novel triazolyl-functionalized chitosan derivatives with different chain lengths of aliphatic alcohol substituent: Design, synthesis, and antifungal activity

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