Chitin amino-groups

Plant stmctural material is the polysaccharide cellulose, which is a linear P (1 — 4) linked polymer. Some stmctural polysaccharides iacorporate nitrogen iato thek molecular stmcture an example is chitin, the material which comprises the hard exoskeletons of kisects and cmstaceans. Chitki is a cellulose derivative whereki the OH at C-2 is replaced by an acetylated amino group (—NHCOCH ). Microbial polysaccharides, of which the capsular or extracellular (exopolysaccharides) are probably the most important class, show more diversity both ki monomer units and the nature of thek linkages. 

The rate of in vivo biodegradation of subcutaneous implanted films was very high for chitin compared with that for deacetylated chitin. No tissue reaction was foimd with highly deacetylated chitosans, although they contained abundant primary amino groups [240]. 

Numerous substituted derivatives of chitin and chitosan are known [67] some important examples are shown in Scheme 10.9. The possibility of forming either anionic (5,7,8,11) or cationic (9,12) derivatives should be noted. The O-carboxymethyl (5) and N-carboxymethyl (11) polymers are of particular interest as they have stronger complex-forming capabilities with metal ions than either unsubstituted chitosan or EDTA [65]. In practice, derivatives formed by substitution via the 2-amino group of chitosan are more common than those substituted via the 6-hydroxy position of the glucopyranose grouping [65]. 

Chitin and chitosan derivatives have also been studied as blood compatible materials both in vivo and in vitro [520], Anticoagulant activity was greatest with O sulfated N acetyl chitosan, followed by N,0 sulfated chitosan, heparin, and finally sulfated N acetyl chitosan. The lipolytic activity was greatest for N,0 sulfated chitosan followed by heparin. The generally poor performance of chitosan was attributed to polyelectrolyte complexes with free amino groups present on the membrane surface. The O sulfate or acidic group at the 6 position in the hexosamine moiety was identified as the main active site for anticoagulant activity. 

A number of studies have examined the antioxidant activities of chitosan from various sources. Park et al. (2004a) prepared three kinds of partially deacetylated hetero-chitosans such as 90% deacetylated, 75% deacetylated, and 50% deacetylated chitosan from crab chitin, and their antioxidant properties were measured using electron spin resonance spectrometry. Park and coworkers found that their antioxidant activities were dependent on the DD, and the 90% deacetylated chitosan showed the highest free radical scavenging activities. Yen et al. (2008) also found that a sample with more amino groups at the C-2 position showed the highest antioxidant activity. Tomida et al. (2009) examined the protective effects of seven different MW chitosans on plasma protein from oxidation by peroxyl radicals. In the ability to protect plasma protein from... 

Chitin is a linear homopolysaccharide composed of Af-acetylglucosamine residues in /3 linkage (Fig. 7-18). The only chemical difference from cellulose is the replacement of the hydroxyl group at C-2 with an acety-lated amino group. Chitin forms extended fibers similar to those of cellulose, and like cellulose cannot be digested by vertebrates. Chitin is the principal component of the hard exoskeletons of nearly a million species of arthropods—insects, lobsters, and crabs, for example— and is probably the second most abundant polysaccharide, next to cellulose, in nature. 

Chitin consists of chains of cyclic carbohydrate molecules linked together and it is basically the same as cellulose except that in place of a hydroxy group (OH) on the rings there is an acetylamino group (NHCOCHj). Like cellulose, chitin is insoluble in water. Removal of the acetyl part to leave the amino group produces a modified chitin which can be used to remove the cloudiness of beers and fruit juices. 

Chitin, the principal component of the exoskeleton of arthropods (insects and Crustacea), consists of N-acetyl-o-glucosamine residues in a P-1,4-linkage. The only chemical difference from cellulose is that the substituent at C-2 is an acetylated amino group instead of a hydroxyl group. 

Natural polysaccharides available on an industrial scale include polymers with anionic functions, like alginates (carboxylic groups) or carrageenans (sulfonic groups) derived from seaweed, or with cationic functions, like as chitosan (amino groups), obtained by deacetylation of chitin from seafood shells (Fig. 1). 

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