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Organic Synthesis and Application about Chitosan Derivatives

Author: ZhaoJing
Tutor: ??YueZhiZhou
School: Wuhan University of Technology
Course: Applied Chemistry
Keywords: 2-deoxy-D-glucose 1,3,4,6-tetraacetyl-2-amino-D-glucose chitosin organic synthesis microsphere the release behavior kinetics in vitro
CLC: O629.1
Type: Master's thesis
Year: 2005
Downloads: 280
Quote: 0
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Abstract


The glucide is a class of organic substances with a wide range of chemistry structures and biological functions. Different kinds of monosaccharide can form oligosaccharide and poly -saccharide. Additionally they can combine with protein, lipid and organic small molecule to form glucoconjugates. These complicated glucide compounds participate in many important biological activities of the body.A lot of monosaccharides have antibacterial, antivirus and anticancer activity. 2-deoxy-D-glucose is a natural monosaccharide and the analogy of glucose. In the metabolism process of glucose it competes with glucose to integrate with hexosidase, then inhibit glucose metabolism. It can effectively inhibit herps simplex virus and RNA、 DNA enveloped viruses like as influenza, Sars, AIDS and interfere with the synthesis of virus glucoprotein. l,3,4,6-tetraacetyl-2-amino-D-glucose is the main derivative of 2-amino-D-glucose which possesses some biological activities including antitumor, antivirus and antiimpaludism. It is also the intermediate substance in the synthesis of glucosides and glucoconjugtes.This thesis was divided into three parts. The first was the preparation of 2-deoxy-D-glucose from chitosin by degradation and amino protection followed by acetylation, deprivation of amino to form 2- chlorine-2-deoxy-D-glucose and reduction. The main advantage of this method was to use chitosin as the raw material which was a reproducible ocean resource to reduce the cost. The second part was the preparation of l,3,4,6-tetraacetyl-2-amino-D-glucose. 4-methyl-2-pentanone protected the amino as a new amino protective agent to form the Schiff base, followed by acetylated the rest hydroxyl in one pot. The condition of deprotection was mild and easy. Finally the microsphere of 2-deoxy-D-glucose loaded with polylactide was prepared and the release behavior kinetics in vitro was studied. The pharmacy of 2-deoxy-D-glucose as a potential drug hadn’t been researched.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Natural compounds > Carbohydrates, sugars
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