Chito-oligosaccharide

Fig. I.—Hypothetical Transition State for the Cleavage of the Glycosidic Bond of a (GlcNAc) Chito-oligosaccharide Chain at Sub-Site D of the Substrate Binding Cleft of Lysozyme (from Ref. 65, with Permission).

Like 2-amino-2-deoxy-D-glucose, the chito-oligosaccharides having unsubstituted 2-amino groups do not bind to WGA, due, presumably, to repulsion of their positively charged -NH3+ groups.128-498... 

Squaric acid esters (Fig. 5a) sometimes are used to link glycans to proteins (52, 54—56). A-Acetyl-chito-oligosaccharides were linked to silk fibroin by reacting solubilized siUc fibroin with cyanuric chloride-activated oligosaccharides (Fig. 5b). 

Nagahori N, Lee RT, Nishimura S, Page D, Roy R, Lee YC. Inhibition of adhesion of type 1 fimbriated Escherichia coli to highly mannosylated ligands. ChemBioChem. 2002 3 836-844. Gotoh Y, Tsukada M, Aiba S, Minoura N. Chemical modification of silk fibroin with N-acetyl-chito-oligosaccharides. Int. J. Biol. Macromol. 1996 18 19-26. 

Tsukada, S. and Inoue, Y. 1981. Conformational properties of chitooligosaccharides—titration, optical rotation and C-13 NMR-studies of chito-oligosaccharides. Carbohydr. Res. 88, 19-38. 

This combination of van der Waals and hydrogen-bond interactions is adequate to explain the basic features of the interaction between hevein and chito-oligosaccharides. Indeed, this type of structure is fairly stable, as demonstrated by its persistence in water-dimethyl sulfoxide (Me2SO) mixtures.Thus NMR-spectroscopic measurements demonstrated complexation between hevein and (G1cNAc)3, albeit with progressively diminished affinity by more than 1.5 orders of magnitude, in mixtures of water and up to 50% Me2SO. ... 

Glycoproteins. — Pseudoglycoproteins have been synthesized by treating proteins with carbohydrates (see e.g.. Tables 1-5), chiefly for use in affinity chromatography. Oligosaccharides coupled to bovine serum albumin for use as immunogens include chito-oligosaccharides (also coupled to cytochrome c), lactose covalently attached to S-ethoxycarbonyloctanol, 4-isothiocyanato-... 

H S Seong, J P Kim and S W Ko, Synthesis of quaternary ammonium derivative of chito-oligosaccharide as antimicrobial agent for cellulosic fibers . Textile Res J, 1999 69 483-488. 

Bahrke, S, J. M. Einarsson, J. Gislason, S., Letzel, J. Peter-Katalinic, and M. G. Peter. 2002. Sequence analysis of chito-oligosaccharides by matrix-assisted laser desorption ionization postsource decay mass spectrometry. Biomacromolecules 3 696-704. 

Becker, H. R, A. Thellend, A. Piffeteau, and A. Vidal-Cros. 2006. Chemoenzymatic synthesis of stable isotope labelled UDP-N-[ H]-acetyl-glucosamine and [ H]-acetyl-chito-oligosaccharides. Glycoconj. J. 23 6S1-692. 

Boer, H., N. Munck, J. Natunen, G. et al. 2004. Drfferential recognition of animal type P-4-galactosylated and a-3-fucosylated chito-oligosaccharides by two family 18 chitmases from Trichoderma hanianum. Glycobiology 14 1303-1313. 

Chen, Y. Y., C. Y. Cheng, T. L. Haung, and Y. K. Li. 2005. Achitosanase from Paecilomyces lilacinus with binding affinity for specific chito-oligosaccharides. Biotechnol. Appl. Biochem. 41 145-150. 

Dong, Y H. Wang, W. Zheng, Y. Zhao, D. Bi, L. Zhao, and X. Li. 2004. Liquid crystaUine behaviour of chito-oligosaccharides. Carbohydr. Polym. 57 235-240. 

Letzel, M. C., B. Synstad, V. G. H. Eijsink, J. Peter-KataUnic, and M. G. Peter. 2000. Lihraries of chito-oligosaccharides of mixed acetylation patterns and their interactions with chitinases. Adv. Chitin Sci. 4 545-552. 

Schanzenbach, D. and M. G. Peter. 1997. NMR spectroscopy of chito-oligosaccharides. In Chitin Handbook, eds. R. A. A. Muzzarelli and M. G. Peter, pp. 199-204. Grottammare, Italy European Chitin Society. 

Enzymatic depolymerization seems to be a better method to prepare chito oligosaccharides. Microorganisms have been found to possess chitosanase activity. Among bacteria, Bacillus and Streptomyces strains are most often studied. Studies on fungal chitosanase are less reported (Cheng and Li 2000). 

Heggset, E.B., Hoell, LA., Kristoffersen, M., Eijsink, V.G., and Virum, K.M. 2009 Degradation of chitosans with chitinase G from Streptomyces coelicolor A3(2) Production of chito-oligosaccharides and insight into subsite specificities. Biomacromolecules 10 892-899. 

Usui, T., Matsui, H., and Isobe, K. 1990. Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfate. Carbohydr. Res. 203 65-77. 

Chitin, a p-1,4 polymer of A-acetyl-o-glucosamine (GlcNAc), is the second abundant biopolymer found in nature after cellulose (Muzzarelli 1999). This natural resource is relatively easily accessible, for example, as crab and shrimp shell waste. A-acetyl-chito-oligosaccharides and chito-oligosaccharides have varied biological functions and many potential applications in a wide range of fields (Tokoro et al. 1988, Hirano and Nagao 1989). To obtain enzymes that can be applied... 

Vishu Kumar, A. B., Varadaraj, M. C., Gowda, L. R., and Tharanathan, R. N. 2005. Characterization of chito-oligosaccharides prepared by chitosanolysis with the aid of papain and Pronase, and their bactericidal action against Bacillus cereus and Escherichia coli. Biochem. J. 391 167-175. 

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