硫代吡喃糖苷的合成及qcm分析其与cona的相互作用-synthesis of thiopyranoside and qcm analysis of its interaction with cona.docx

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2018-05-27 发布于上海
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硫代吡喃糖苷的合成及qcm分析其与cona的相互作用-synthesis of thiopyranoside and qcm analysis of its interaction with cona.docx

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硫代吡喃糖苷的合成及qcm分析其与cona的相互作用-synthesis of thiopyranoside and qcm analysis of its interaction with cona

AbstractCarbohydrate/proteininteractionsarecruciallyimportantinmanybiologicalprocesses,andthushavebeengreatlyconcerned.Toinvestigatethoseinteractions,bothvariouscarbohydratetargetsmainlysuppliedbycarbohydratesynthesis,andpowerfulanalysismethods,suchasSPR,ITC,QCMandsoon,areindispensable.Thio-containingglycosidesareoftenappliedinthesynthesisofoligosaccharides.Manyofthemhavebeendirectlyusedasdrugsoraspotentialtherapeuticprototypesinthetreatmentofavarietyofpathologicalconditions.Moreimportantly,thio-containingglycosideshavegreatadvantageswhenappliedinDynamicCombinatorialChemistry(DCC)sincetheycanofferaconsequentsetofreversiblereactionsatverymildconditions.Thus,synthesisofthio-containingglycosidesandinvestigationoftheirinteractionstoproteinsareofconsiderablecurrentresearchinterests.Inthepresentstudies,bytheapplicationofdoubleparallelanddoubleserialinversion,thiolanalogsofD-pyranosideswereefficientlysynthesized.Withthecombinationofotherdevelopedsyntheticmethods,9thiolanalogsofD-mannopyranosideswerefinallyacquired.Theproteinrecognitionpropertiesofthese9thio-containingmannosideswerethenevaluatedinacompetitionbindingassaywiththemodellectinConAbyQCM.EC50valueswereestimatedbynon-linearregression.Tooursurprise,Methylα-D-mannopyranosidedisplayedsignificantlowerbindingaffinitytowardsConAthanits2-thioanalog.Resultswereinagreementwithknownbindingaffinitieswherethe4-thio-analog,6-thio-analogandβ-D-derivativesofMethylα-D-mannopyranosideareineffective.3-thio-analogshowsslightlylowerbindingaffinities.Keywords：Thio-containingglycoside,Thio-containingmannoside,QCM,ConA目录摘要....................................................................................................................IABSTRACT.........................................................................................................II1绪论1.1糖的生物学意义.............................................................................................11.2糖和蛋白的相互识别作用......................................................................