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Part I. Synthesis of fluorinated astaxanthins. Part II. Synthesis and properties of sterically hindered 1,4-diphenyl-1,3-butadienes

Posted on:1998-03-31Degree:Ph.DType:Dissertation
University:University of Hawai'iCandidate:Liu, JinFull Text:PDF
GTID:1461390014474852Subject:Chemistry
Abstract/Summary:
Part I. All-trans-14-F-astaxanthin, all-trans-10-F-astaxanthin, all-trans-10,10{dollar}spprime{dollar}-F,F{dollar}spprime{dollar}-astaxanthin and all-trans-10-F-3{dollar}sp prime{dollar}-hydroxy-{dollar}beta,beta{dollar}-carotene-4,4{dollar}spprime{dollar}-dione were synthesized by applying the {dollar}rm Csb{lcub}15{rcub}+Csb{lcub}10{rcub}+Csb{lcub}15{rcub}{dollar} synthetic approach. The fluorinated analogs characterized by UV-Vis, {dollar}sp1{dollar}H-NMR, {dollar}sp{lcub}19{rcub}{dollar}F-NMR, {dollar}sp{lcub}13{rcub}{dollar}C-NMR and HR-MS spectroscopies bound with the apoprotein which was isolated from the carapace of lobster to form the blue carotenoid-protein complexes. The fluorinated analogs are good anti-cancer drug candidates and also will be useful for the future studies of carotenoid-protein interactions.; Part II. A sterically hindered 1,4-diphenyl-1,3-butadiene has been synthesized. The unusual UV red-shift property of this compound was observed. The crystal structure of this sterically hindered molecule revealed the highly crowded nature of this compound when the two phenyl rings are forced into an orientation nearly parallel to each other by twisting at both diene single bonds {dollar}({lcub}sim{rcub}50spcirc){dollar} and the diene double bonds {dollar}({lcub}sim{rcub}28spcirc).{dollar} The non-covalent interaction between the two phenyl rings is believed to contribute to the unusual UV red-shift property of the sterically hindered 1,4-diphenyl-1,3-butadiene.
Keywords/Search Tags:Sterically hindered, Part, Fluorinated, 4-diphenyl-1, {dollar}
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