Chitooligosaccharides: Synthesis, characterization and applications

Polymer Science Series A (Impact Factor: 0.67). 01/2011; 53(7):583-612. DOI: 10.1134/S0965545X11070066

ABSTRACT Chitosans with high degree of polymerization and molecular weight exhibit poor aqueous solubility which is an impediment in
their applicability. The low molecular weight chitosans (LMWCs) and chitooligosaccharides (COSs) can be used to avoid this
hurdle. The development of an efficient process for reducing the molecular weight of chitosan, without altering its chemical
structure, is of great interest to produce tailormade chitosans of varying Degree of Acetylation (DAs) and Degree of Polymerization
(DPs). The production of well-defined COS-mixtures, or even pure COS, is of great interest since these oligosaccharides are
thought to have several interesting bioactivities and applications. For this proper delineation of their characteristics is
needed. Hence it is our attempt to provide an overview of difffernt methods and techniques of their production and characterization.
Several methods viz. depolymerization under the action of reagents, enzymes, high energy impact and combinations thereof have
been employed to get COS by depolymerization of high molecular weight chitosans. Acid hydrolysis (hydrochloric, nitrous, phosphoric
acid, hydrogen fluoride) and oxidative reductive depolymerization (mediated by peroxide, ozone, and persulfate) are important
routes for synthesis of COSs. These oligomers can be produced from chitin or chitosan as a starting material by enzymatic
conversions. For this, numbers of enzymes have been used. Depolymerization under high energy impact and recombinant approaches
are also being tried for production of COSs. LMWC and COS, like parent chitosan, can be used for drug delivery and gene delivery.
The efficient and productive processes are needed for separation of COSs into its components or mixture of defined characters.
The characterization of COS can be carried out by chromatographic and spectroscopic techniques. Importantly COSs display an
array of biological activities as antimicrobial, anticancer/antimetastatic, wound healing acceleration, immunostimulation,
apoptosis induction or inhibiton, antioxidant, enzyme inhibiton, antihyperlipidemic, antidiabetic, chemoprevention, and many
more. A few of the biological actions are reported only sporadically where as some are persistently taken up by the scientific
fraternity to substantiate the claims and propose possible mechanisms of action. However there remains the disagreement of
results on COS activities. The disagreements can arise due to poor and variable reporting of the properties of COS such as
used in the studies as molecular weight, degree of acetylation, molecular weight distribution, and the pattern of N-acetylation
etc. With production of COS of well defined characters it might be possible to understand the modes of actions of COS in better

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    ABSTRACT: Chitosan of 24% degree of acetylation was depolymerized by a mixture of cellulase, alpha amylase, and proteinase to give the title oligosaccharides. The removal of products by membrane separation permitted yield maximization of products having degree of polymerization in the 3-10 range.
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    ABSTRACT: Commercial chitosans were subjected to controlled acid hydrolysis and their degrees of deacetylation (DD), molecular size and rheological flow profiles determined (pre- and post-hydrolysis) by 1H-NMR spectroscopy, high-performance size-exclusion chromatography and rheometry, respectively. Hydrolysis resulted in DD increases between 4 and 11%. Unhydrolysed chitosans had Mw and Mn values in the ranges 700–1200 and 130–210 kDa, respectively. Chitosan with the smallest initial molecular size averages had the smallest averages after hydrolysis; however, a chitosan with an intermediate initial molecular size proved to be most resistant to hydrolysis. Molecular size trends were paralleled by zero shear viscosity (η0) measurements determined by application of the Williamson model to rheological flow profile data. Viscosity is obviously related to molecular size, but does not necessarily reflect relative ease of hydrolysis, since specific hydrolysis conditions affect structurally similar polysaccharides in different ways (in terms of rate of depolymerisation and de-N-acetylation, etc), which are not simply due to differences in molecular size profiles pre-hydrolysis. Copyright © 2005 Society of Chemical Industry
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May 22, 2014