(I) Development of an Inexpensive Carbohydrate Derivative Used as a Chiral Auxiliary in the Synthesis of alpha-Hydroxy Carboxylic Acids. (II) Synthesis of a Potential Carrier for Copper Ions Designed to Be Transported by P-Glycoprotein.

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dc.contributor.advisor Binghe Wang, Committee Chair en_US
dc.contributor.advisor Daniel L. Comins, Committee Member en_US
dc.contributor.advisor Jonathan S. Lindsey, Committee Member en_US
dc.contributor.advisor Suzanne T. Purrington, Committee Member en_US
dc.contributor.author Ballard, Charles Eric en_US
dc.date.accessioned 2010-04-02T19:03:20Z
dc.date.available 2010-04-02T19:03:20Z
dc.date.issued 2003-11-14 en_US
dc.identifier.other etd-11122002-173847 en_US
dc.identifier.uri http://www.lib.ncsu.edu/resolver/1840.16/4893
dc.description.abstract 1. Development of an Inexpensive Carbohydrate Derivative Used as a Chiral Auxiliary in the Synthesis of alpha-Hydroxy Carboxylic Acids Protected alpha-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate (alpha-hydroxy acetate) enolates using a D-fructose-derived chiral auxiliary. The new chiral center was assigned the R configuration based on comparisons of optical rotations and on one crystal structure analysis. This alkylation methodology is compatible with several hydroxyl protecting groups. The free hydroxy acids were obtained upon removal of the protecting group from the hydroxyl functionality followed by saponification. 2. Synthesis of a Potential Carrier for Copper Ions Designed to Be Transported by P-Glycoprotein Poisoning by heavy metals has traditionally been treated with a handful of nonspecific, highly polar chelating agents. Although the present set of chelators has proven to be valuable as therapeutics, their lack of specificity sometimes results in leaching of essential minerals and their high polarity limits their excretion, such that the metal-chelate complexes are primarily removed by the kidneys. We have developed a potential transporter for copper ions, consisting of a chelator conjugated to a P-glycoprotein transporter substrate. We hypothesize that upon complexation to copper, the complex can be removed by the P-glycoprotein active transporter. Assays that will determine the metal-binding and biological transport properties of the conjugates are planned for later. en_US
dc.rights I hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to NC State University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report. en_US
dc.subject hydroxy acid en_US
dc.subject metal toxicity en_US
dc.subject P-glycoprotein en_US
dc.subject chiral auxiliary en_US
dc.subject enolate alkylation en_US
dc.subject carbohydrate en_US
dc.title (I) Development of an Inexpensive Carbohydrate Derivative Used as a Chiral Auxiliary in the Synthesis of alpha-Hydroxy Carboxylic Acids. (II) Synthesis of a Potential Carrier for Copper Ions Designed to Be Transported by P-Glycoprotein. en_US
dc.degree.name PhD en_US
dc.degree.level dissertation en_US
dc.degree.discipline Chemistry en_US


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