Preparation and graft copolymerisation of thiolated β-chitin and chitosan derivatives

Munro, Natasha H.; Hanton, Lyall R.; Moratti, Stephen C.; Robinson, Brian H.

doi:10.1016/j.carbpol.2009.04.018

Cited by 9 publications

(7 citation statements)

References 22 publications

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“…The degree of substitution of TCT is 0.93, which means that there are 93% of hydroxyl groups at C-6 being displaced by tosyl groups. The DS of DTCT is 1.2 based on elemental analysis, i.e., the C3-OH moiety was partially substituted, which was consistent with the literature [ 25 ]. Accurately, in DTCT, 3,6-ditosyl-chitin accounts for 20% and 6-tosyl-chitin for the remaining 80% by calculation.…”

Section: Resultssupporting

confidence: 87%

Synthesis of Novel Chitin Derivatives Bearing Amino Groups and Evaluation of Their Antifungal Activity

Zhang

Luan

et al. 2018

Marine Drugs

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Chemical modification is one of the most effective methods to improve the biological activity of chitin. In the current study, we modified C3-OH and C6-OH of chitin (CT) and successfully synthesized 6-amino-chitin (NCT) and 3,6-diamino-chitin (DNCT) through a series of chemical reactions. The structure of NCT and DNCT were characterized by elemental analyses, FT-IR, 13C NMR, XRD, and SEM. The inhibitory effects of CT, NCT, and DNCT against six kinds of phytopathogen (F. oxysporum f. sp. cucumerium, B. cinerea, C. lagenarium, P. asparagi, F. oxysporum f. niveum, and G. zeae) were evaluated using disk diffusion method in vitro. Meanwhile, carbendazim and amphotericin B were used as positive controls. Results revealed that 6-amino-chitin (NCT) and 3,6-diamino-chitin (DNCT) showed improved antifungal properties compared with pristine chitin. Moreover, DNCT exhibited the better antifungal property than NCT. Especially, while the inhibition zone diameters of NCT are ranged from 11.2 to 16.3 mm, DNCT are about 11.4–20.4 mm. These data demonstrated that the introduction of amino group into chitin derivatives could be key to increasing the antifungal activity of such compounds, and the greater the number of amino groups in the chitin derivatives, the better their antifungal activity was.

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Section: Resultssupporting

confidence: 87%

Synthesis of Novel Chitin Derivatives Bearing Amino Groups and Evaluation of Their Antifungal Activity

Zhang

Luan

et al. 2018

Marine Drugs

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“…The degree of substitution (DS) is shown in Table , as determined by the S/N (TCT and DTCT) or C/N (other derivatives) ratio obtained from the elemental analysis. The DS of DTCT was 1.18, indicating that the C3OH moiety is substituted, which is consistent with the literature . The target product was then prepared from TCT.…”

Section: Resultssupporting

confidence: 86%

“…The spectra of tosyl CT contained typical peaks attributed to the tosyl group at 3070 cm −1 (tosyl CH), 1176 cm −1 (SO 2 ), 1601 cm −1 (aromatic CC), and 813 cm −1 (phenylene), indicating successful tosyl substitution …”

Section: Resultsmentioning

confidence: 99%

“…The other method, reported by Morita, used a LiCl/dimethyl acetamide solvent system to obtain only 6‐TCT . TCT has been obtained with a high degree of substitution in alkaline solution (the Kurita method), with some authors isolating 6‐TCT and others obtaining 3,6‐ditosyl‐chitin . We speculated that one important factor influencing the degree of substitution was the source of CT.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Antifungal Activity of N‐Quaternized and N‐Diquaternized Chitin Derivatives

et al. 2018

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To improve the bioactivity of chitin (CT), novel N-quaternized (QCT), and N-diquaternized (DQCT) CT derivatives are synthesized through a series of reactions from CT. The derivatives are characterized using elemental analysis, FTIR, and 13 C NMR. In addition, the inhibitory effects of the compounds against three fungi (B. cinerea, F. oxysporum, and P. asparagi) are tested. The inhibitory indices of CT, QCT, and DQCT are 12-15%, 63-73%, and 74-89%, respectively, at 1.0 mg mL À1 . The antifungal activities are in the order of DQCT > QCT > CT, which correlated with the number of quaternized groups. Based on these results, it is concluded that the antifungal activity of CT is improved by the introduction of quaternized groups on CT backbone.

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“…The recently described methods for chitin tosylation are an alternative to that described by Kurita et al., where deacetylation was observed . Several nucleophiles such as sodium iodide, sodium azide, or potassium thioacetate were used to replace the tosyl group to produce iodo‐, azido‐, or mercapto‐chitin and chitosan derivatives, respectively. In fact, this methodology can be applied to produce relevant materials, such as a chitosan derivative possessing a cyclodextrin at O‐6, which was obtained by nucleophilic substitution of the tosyl group by an ethylenediamine‐substituted cyclodextrin.…”

Section: Selective Modificationmentioning

confidence: 99%

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

Carvalho

Queda

Santos

et al. 2016

Chemistry An Asian Journal

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Chitin and chitosan are attractive biopolymers with enormous structural possibilities for chemical modification, creating platforms for new chemical entities with a broad scope of applications, ranging from material science to medicine. During the last few years, incredible efforts have been dedicated to the regioselective modification of these biopolymers paving the way for improved properties and tailored activities. Herein, the most recent advances in chitin/chitosan regioselective modification, reaction conditions, selectivity, and the impact on its applications are highlighted. Moreover, the recent focus on chitooligosaccharides, their regioselective and chemoselective functionalization, as well as their role in biological studies, including molecular recognition with several biological targets are also covered.

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Preparation and graft copolymerisation of thiolated β-chitin and chitosan derivatives

Cited by 9 publications

References 22 publications

Synthesis of Novel Chitin Derivatives Bearing Amino Groups and Evaluation of Their Antifungal Activity

Synthesis of Novel Chitin Derivatives Bearing Amino Groups and Evaluation of Their Antifungal Activity

Synthesis, Characterization, and Antifungal Activity of N‐Quaternized and N‐Diquaternized Chitin Derivatives

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

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