N-acetylation in chitosan and the rate of its enzymic hydrolysis

doi:10.1016/0142-9612(89)90066-5

Biomaterials

Volume 10, Issue 8, October 1989, Pages 574-576

https://doi.org/10.1016/0142-9612(89)90066-5 Get rights and content

Abstract

Partially N-acetylated derivatives (degree of substitution (d.s.) 0.2, 0.4, 0.6 and 0.8 for N-acetyl) of chitosan were prepared from prawn shell chitosan, and their susceptibility towards a lysozyme from hen egg-white, three microbial chitinases and a chitinase from potato skins was examined. The partially N-acetylated derivatives (d.s. 0.4-0.8 for N-acetyl) were 1.5–4.0 times more digestible than N-acetylchitosan (d.s. 1.0 for N-acetyl), and their enzymic hydrolysis rate is controlled by the d.s. for N-acetyl group. These data suggest that chitosan is usable as a digestible material in the biomedical and biotechnological fields.

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There are more references available in the full text version of this article.

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Biopolymers like cellulose, polysaccharides, chitosan, starch, chitin, and alginates have sparked an increasing curiosity in creating natural replacements for synthetic polymers during the last several decades. Chitin is a major part of fungi’s cell walls, the crustaceans’ exoskeletons, like lobsters, crabs, and shrimps, cephalopod beaks, the radulae of mollusks, and fish and lissamphibians scales. Since the late 1970 s, biopolymer chitosan has gathered interest in basic science and applied research due to its incredible macromolecular framework, physicochemical properties, and biological activities, which differ from those of synthetic polymers. Chitin and derivatives thereof have practical usages in chemistry, the agriculture sector, medicine, cosmetics, as well as textile and paper industries. Chitosan has also received a lot of recent interest in the fields of dentistry, ophthalmology, veterinary science, biomedicine, the drink industry, hygiene and personal care, catalysis, chromatography, sewage treatment, and biotechnology. Numerous fundamental investigations have been conducted on chitin and chitosan. This article presents a short compact summary of research over the last two decades in an attempt to highlight the works on chitin and chitosan applications.
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The biodegradation behavior of the hydrogels was evaluated in terms of weight loss over a period of 21 days, in conditions mimicking the environment of infected wounds: lysozyme solution of pH 8.5 at 37 °C (Fig. 13) [4]. The lysozyme was chosen due to its presence in wound fluid, and its ability to hydrolyze the chitosan into oligomers [59,60]. The most promising samples for in vivo applications were chosen for this study (Fig. 13).
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We propose a novel approach relied on high-resolution solid-state ¹³C NMR spectroscopy to quantify the crystallinity index of chitosans (Ch) prepared with variable average degrees of acetylation ( $\bar{D A}$ ) from 5% to 60 % and average weight molecular weight ( ${\bar{M}}_{w}$ ) ranged in 0.15 $\times$ 10⁶ g mol⁻¹–1.2 $\times$ 10⁶ g mol⁻¹. The Dipolar Chemical Shift Correlation (DIPSHIFT) curve of the C(6)OH segment revealed increased mobility dynamic, which induced different distribution from trans-to-gauche conformations in relation to C(4). Indeed, ¹H-¹³C Heteronuclear Correlation (2D HETCOR) showed that distinguished C4 chemical shifts correlates with the same aliphatic protons. The short-range ordering can be assigned to C4/C6 signals on ¹³C CPMAS and, for our case, the deconvolution procedure between disordered and ordered phases revealed increasing crystallinity with $\bar{D A}$ , as confirmed by SVD multivariate analysis. This work extended the knowledge regarding the use of ¹³C CPMAS technique to predict the crystallinity of chitosans without the use of amorphous standards.
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Citation Excerpt :
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Biomaterials

Abstract

References (12)

The effects of N-substitution of chitosan and the physical form of the products on the rate of hydrolysis by chitinase from Streptomyces griseus

Carbohydr. Res.

Selective -acylation of chitosan

Carbohydr. Res.

A modified colorimetric method for the estimation of N-acetylamino sugars

J. Biol. Chem.

Chitosanase. A novel enzyme

Nature (London), New Biol.

Preparation of d-glucosamine oligosaccharides by the enzymic hydrolysis of chitosan

Agric. Biol. Chem.

A biomédical use of chitin

Jinko Zoki

Cited by (219)

Advancement of chitin and chitosan as promising biomaterials

Chitosan crosslinking with a vanillin isomer toward self-healing hydrogels with antifungal activity

Intermolecular interactions of chitosan: Degree of acetylation and molecular weight

Chitin, chitosan, and their derivatives

Evaluation of chitosan crystallinity: A high-resolution solid-state NMR spectroscopy approach

Synthesis, characterization, and the antioxidant activity of the acetylated chitosan derivatives containing sulfonium salts

CommunicationN-acetylation in chitosan and the rate of its enzymic hydrolysis

Abstract

Carbohydr. Res.

Carbohydr. Res.

J. Biol. Chem.

Chitosanase. A novel enzyme

Nature (London), New Biol.

Preparation of d-glucosamine oligosaccharides by the enzymic hydrolysis of chitosan

Agric. Biol. Chem.

A biomédical use of chitin

Jinko Zoki

Communication
N-acetylation in chitosan and the rate of its enzymic hydrolysis