Syntheses of photoactivatable and fluorescent labeled lipids.
Item
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Title
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Syntheses of photoactivatable and fluorescent labeled lipids.
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Identifier
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AAI3037416
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identifier
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3037416
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Creator
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Li, Guoqing.
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Contributor
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Adviser: Robert Bittman
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Date
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2002
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic
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Abstract
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This thesis describes synthetic sequences that were used to prepare new photoactivatable and fluorescent lipid probes.;Chapter 1 describes the syntheses of photoactivatable lipid probes of phosphatidylcholine (PC) and ceramide. In these probes, a trifluoromethyldiazirine (TID) group, which is a carbene precursor for covalent labeling, was made from a trifluoroacetyl group via several steps. Stille coupling reaction was employed to convert an iodo group to a tin-substituent and then, and iododestannylation reaction was used to convert tin-substituted probe to an iodine-labeled probe.;Chapter 2 presents the syntheses of novel photoactivatable naphthalene-containing PC and ceramide probes. A new PC analog bearing a fluorophore as well as an aryl azide moiety was also synthesized.;Chapter 3 presents the syntheses of two photoreactive analogs of the antitumor ether lipid 1-O-octadecyl-2-O-methyl- rac-glycero-3-phosphocholine (ET-18-OCH3) for the first time. One of the photoactivatable ET-18-OCH3 analogs contained a TID moiety, whereas the other analog did not contain the iodo group.;Chapter 4 describes the syntheses of fluorescent analogs of cholesterol and cholesteryl esters in which the fluorophore is located in the sterol side chain.;Sphingosine is an important bioactive lipid and is also the backbone of sphingolipids such as sphingomyelin, cerebrosides, and gangliosides. In Chapter 5, a highly concise synthetic route to D-erythro -sphingosine and a short-chain analog of sphingosine was developed employing a sulfoxide intermediate, followed by dehydrosulfenylation, affording a synthon that is readily converted to naturally occurring (2S,3 R,4(E))-sphingosine.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
