Syntheses of sphingolipid analogs.
Item
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Title
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Syntheses of sphingolipid analogs.
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Identifier
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AAI3231962
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identifier
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3231962
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Creator
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Liu, Yidong.
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Contributor
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Adviser: Robert Bittman
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Date
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2006
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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 dissertation presents the asymmetric syntheses of sphingolipid analogs, including (a) fluorescent lactosylceramide stereoisomers, (b) sphingosine 1-phosphate-d8, (c) deuterated sphingomyelin analogs, and (d) (2S,3S)-3-fluoro-4,5-dihydrosphingosine and (2S,3R)-1-fluorosphingosine.;Chapter 1 presents the synthesis of three stereoisomers of BODIPY-LacCer: (2R,3R)-, (2S,3 S)-, and (2R,3S)-. These analogs will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake in living cells.;Chapter 2 presents the synthesis of sphingosine 1-phosphate- d8 which is used as an internal standard for quantitative analysis of serum sphingosine 1-phosphate.;Chapter 3 presents the first synthesis of four deuterated sphingomyelin analogs: N-palmitoyl-d31-SM, 4,5-dihydro- N-palmitoyl-d31-SM, N-palmitoyl-3,3-d 2-SM, and N-palmitoyl-2,2,3,3,4,4-d6-SM. These analogs will be used to study the conformation of the sphingomyelin (SM)-water interface in bilayers by 2H nuclear magnetic resonance (NMR) spectroscopy.;Chapter 4 presents the synthesis of (2S,3S)-3-fluoro-4,5-dihydrosphingosine and (2S,3R)-1-fluorosphingosine. The phosphorylated derivatives of these compounds would be of interest in a study of binding to sphingosine 1-phosphate receptors.
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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.
