Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators

Low molecular weight gelators (LMWGs) are small molecules that are capable of entrapping solvents to form a gel in organic solvents or aqueous solution. These compounds rely solely on noncovalent forces to form the fibrous networks necessary to entrap a variety of solvents. The organogels and hydrog...

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Main Author: Cheuk, Sherwin
Format: Others
Published: ScholarWorks@UNO 2008
Subjects:
Online Access:http://scholarworks.uno.edu/td/868
http://scholarworks.uno.edu/cgi/viewcontent.cgi?article=1848&context=td
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spelling ndltd-uno.edu-oai-scholarworks.uno.edu-td-18482016-10-21T17:04:51Z Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators Cheuk, Sherwin Low molecular weight gelators (LMWGs) are small molecules that are capable of entrapping solvents to form a gel in organic solvents or aqueous solution. These compounds rely solely on noncovalent forces to form the fibrous networks necessary to entrap a variety of solvents. The organogels and hydrogels thus formed could have applications in a variety of fields from environmental to biological to medicinal. Carbohydrates are ideal starting materials to synthesize LMWGs, because of their natural abundance, dense chirality, and biocompatibility. D-Glucose is the most common monosaccharide and D-glucosamine is isolated from natural sources, such as crab shells. Several series of compounds were synthesized using compounds 1-3 as the starting materials. These include esters, carbamates, amides, and ureas. The structure and gelation relationship was analyzed to obtain guidelines for designing new LMWGs. Compound 1 is a simple derivative of D-glucose and its terminal alkynyl esters and saturated carbamates are effective gelators. Compound 2 is a simple derivative of D-glucosamine and its amide and urea derivatives are also effective gelators. Compound 3 is formed from the deoxygenation of D-glucose. 1OOHOOCH3OHOPh2OOHOOCH3NH2OPh3OOHOOHOPh The design, synthesis and gelation properties of several classes of sugar based low molecular organo/hydrogelators will be discussed in this thesis in chapters 2, 3, and 4. After obtaining highly effective organo/hydrogelators, potential applications of these novel molecular systems can be explored. Some preliminary study on using one of the gelator in enzyme assay has shown that it is possible to utilize the hydrogels to immobilize enzymes. However, future research can explore further on the applications of these gelators. 2008-12-19T08:00:00Z text application/pdf http://scholarworks.uno.edu/td/868 http://scholarworks.uno.edu/cgi/viewcontent.cgi?article=1848&context=td University of New Orleans Theses and Dissertations ScholarWorks@UNO low molecular weight gelator carbohydrates glucose glucosamine fibrillar networks structure-gelation relationships
collection NDLTD
format Others
sources NDLTD
topic low molecular weight gelator
carbohydrates
glucose
glucosamine
fibrillar networks
structure-gelation relationships
spellingShingle low molecular weight gelator
carbohydrates
glucose
glucosamine
fibrillar networks
structure-gelation relationships
Cheuk, Sherwin
Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators
description Low molecular weight gelators (LMWGs) are small molecules that are capable of entrapping solvents to form a gel in organic solvents or aqueous solution. These compounds rely solely on noncovalent forces to form the fibrous networks necessary to entrap a variety of solvents. The organogels and hydrogels thus formed could have applications in a variety of fields from environmental to biological to medicinal. Carbohydrates are ideal starting materials to synthesize LMWGs, because of their natural abundance, dense chirality, and biocompatibility. D-Glucose is the most common monosaccharide and D-glucosamine is isolated from natural sources, such as crab shells. Several series of compounds were synthesized using compounds 1-3 as the starting materials. These include esters, carbamates, amides, and ureas. The structure and gelation relationship was analyzed to obtain guidelines for designing new LMWGs. Compound 1 is a simple derivative of D-glucose and its terminal alkynyl esters and saturated carbamates are effective gelators. Compound 2 is a simple derivative of D-glucosamine and its amide and urea derivatives are also effective gelators. Compound 3 is formed from the deoxygenation of D-glucose. 1OOHOOCH3OHOPh2OOHOOCH3NH2OPh3OOHOOHOPh The design, synthesis and gelation properties of several classes of sugar based low molecular organo/hydrogelators will be discussed in this thesis in chapters 2, 3, and 4. After obtaining highly effective organo/hydrogelators, potential applications of these novel molecular systems can be explored. Some preliminary study on using one of the gelator in enzyme assay has shown that it is possible to utilize the hydrogels to immobilize enzymes. However, future research can explore further on the applications of these gelators.
author Cheuk, Sherwin
author_facet Cheuk, Sherwin
author_sort Cheuk, Sherwin
title Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators
title_short Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators
title_full Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators
title_fullStr Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators
title_full_unstemmed Glucose and Glucosamine Derivatives as Novel Low Molecular Weight Gelators
title_sort glucose and glucosamine derivatives as novel low molecular weight gelators
publisher ScholarWorks@UNO
publishDate 2008
url http://scholarworks.uno.edu/td/868
http://scholarworks.uno.edu/cgi/viewcontent.cgi?article=1848&context=td
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