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Structuralconfirmation
ofoligosaccharides
newlyisolatedfrom
sugerbeetmolasses
Structuralconfirmation
ofoOutlinesBackgroundAchievementExperimentalConclusion&DiscussionOutlinesBackgroundAchievementEBackgroundWhyshouldwedothisexperi-ment?raffinose;otheroligosaccharides;examinedindetailWhatcontributionscouldthestudybring?newoligosaccharides;structurecomfirmed;fullassignmentofthe1H,13Csignals;2D-NMRBackgroundWhyshouldwedothiFouroligosaccharideswereisolatedThestructuralofthemwereconfirmedAchievement1st
Thefirstfullassignmentof1H，13Cand2D-NMRofsaccharide1~4werecarriedout2ndFouroligosaccharideswereisExperimental
DilutedfivetimeswithwaterMOLASSESPreparativeHPLCODScolumn35℃water3.5mL/min60timesDILUTEDMOLASSESMeasuredwithaRefractiveIndexDetectorConcentratedinvacuothenfreeze-driedELUTEDSACCHARIDESPOWDEREDFRACTIONSItoXII
ExperimentalMOLASSESPreparatiExperimentalbyHPAECandTOF-MSanalysesFractionsItoXIIFractionsXI(13.8mg)FractionsIV(51.6mg)FractionsIX(240.0mg)FractionsII(41.1mg)ExperimentalbyFractionsItoXExperimentalcarbon-Celitecolumn10%ethanol(1.8–2.4L)FractionFractionIV
IXFractionII
SACCHARIDE1carbon-Celitecolumn5%ethanol(0.3-1.1L)carbon-Celitecolumn10%ethanol(2.5–2.9L)SACCHARIDE2SACCHARIDE3PreparativeHPLCrepeated60timesrententiontime34.5-35.5FractionXISACCHARIDE4Experimentalcarbon-CelitecoluExperimental1st2nd3rdHPAECSaccharide1~4wereshowntobehomogene-ous,butdidn'tcorrespondtoanyauthenticsaccharidesTOF-MSThepolymerizationwasestablishedas3AcidHydrolyzates→HPLCSaccharides1&2:Glucose,Fructose,Galactose(1:1:1)3&4:Glucose,Fructose(2:1)Methylationandmethanolysis→GLCMethylationwascarriedoutbyHakomorimethodMethanolyzedbyheatingat96℃for30minwith1.5%methanolichydrochloricacidresultExperimental1st2nd3rdHPAECTOF-saccharide31-Kestose1.101.321-Kestose1.471.06Raffinose2.633.741.453.681.29
1.082.55Methyl-1,3,4,6-tetra-O-methyl-D-fructosideMethyl-2,3,4,6-tetra-O-methyl-D-glucosideMethyl-2,3,4-tri-O-methyl-D-glucosideα-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside1.08saccharide31-Kestose1.101-KeExperimentalGlcanomericproton→H-1(δH4.98)methyleneproton→H-6(δC61.25)exhibitedcorrelationpeakstobothH-1andH-2byHMBC→C-3(δC73.8)gavecorrelationpeaktoH-1byCOSY→H-2(δH3.57)exhibitedacorrelationpeaktoH-1byHMBC→C-5(δC72.63)Theremainingmethineprotonincludedinthesamespin-spinnetworkwithH-1→H-4(δH3.44)FruThecharacteristicdoubletsignalinthe1H-NMRspectrum→H-3''(δH4.24)exhibitedacorrelationpeaktoH-3''byCOSY→H-4''(δH4.07)Themethyleneprotoninthesamespin-spinnetworkwithH-3’’,H-4’’,andH-5’’wasassigned→H-6''(δH3.86)gavecorrelationpeaktoH-4''byCOSY→H-5''(δH3.91)exhibitedacorrelationpeaktoH-3’’byHMBC→C-1''(δ62.19)Thequaternarycarbon,whichexhibitedacorrelationpeaktoH-1''byHMBC→C-2''(δ104.57)Saccharide
3ExperimentalGlcanomericprotonExperimentalYourTextHereYourTextHereThearrangementofthesugarresiduesYourTextHereTheanomericproton(H-1’)ofGlc’exhibitedacorrelationpeaktothequaternarycarbon(C-2’’)ofFruGlc(1->6’)toGlc’(1<->2”)toFruTheanomericproton(H-1)ofGlcexhibitedacorrelationpeaktothemethylenecarbon(C-6’)ofGlc’ExperimentalYourTextHereYour
Saccharide3
δCδ
H
JHHGlc198.994.98d3.8272.283.57dd9.4,3.8373.83.76dd10.0,9.4470.293.44dd10.1,1.0572.633.71ddd10.1,5.1,2.2661.253.86dd12.4,2.23.78dd12.4,5.1Glc'1'92.885.45d3.92'71.723.59dd10.2,3.93'73.513.77dd10.2,9.54'70.113.56dd9.5,8.65'72.074.06m6'66.394.05m3.69dd12.6,3.0ExperimentalSaccharide
3Saccharide3δCδHJHHGlConclusion&DiscussionIsolationStructureConfirma-tionPreparativeHPLCcarbon-CelitecolumnchromatographymethylationanalysisMALDI-TOF-MSNMRmeasurementsConclusion&DiscussionIsolatiThankYou!ThankYou!
Structuralconfirmation
ofoligosaccharides
newlyisolatedfrom
sugerbeetmolasses
Structuralconfirmation
ofoOutlinesBackgroundAchievementExperimentalConclusion&DiscussionOutlinesBackgroundAchievementEBackgroundWhyshouldwedothisexperi-ment?raffinose;otheroligosaccharides;examinedindetailWhatcontributionscouldthestudybring?newoligosaccharides;structurecomfirmed;fullassignmentofthe1H,13Csignals;2D-NMRBackgroundWhyshouldwedothiFouroligosaccharideswereisolatedThestructuralofthemwereconfirmedAchievement1st
Thefirstfullassignmentof1H，13Cand2D-NMRofsaccharide1~4werecarriedout2ndFouroligosaccharideswereisExperimental
DilutedfivetimeswithwaterMOLASSESPreparativeHPLCODScolumn35℃water3.5mL/min60timesDILUTEDMOLASSESMeasuredwithaRefractiveIndexDetectorConcentratedinvacuothenfreeze-driedELUTEDSACCHARIDESPOWDEREDFRACTIONSItoXII
ExperimentalMOLASSESPreparatiExperimentalbyHPAECandTOF-MSanalysesFractionsItoXIIFractionsXI(13.8mg)FractionsIV(51.6mg)FractionsIX(240.0mg)FractionsII(41.1mg)ExperimentalbyFractionsItoXExperimentalcarbon-Celitecolumn10%ethanol(1.8–2.4L)FractionFractionIV
IXFractionII
SACCHARIDE1carbon-Celitecolumn5%ethanol(0.3-1.1L)carbon-Celitecolumn10%ethanol(2.5–2.9L)SACCHARIDE2SACCHARIDE3PreparativeHPLCrepeated60timesrententiontime34.5-35.5FractionXISACCHARIDE4Experimentalcarbon-CelitecoluExperimental1st2nd3rdHPAECSaccharide1~4wereshowntobehomogene-ous,butdidn'tcorrespondtoanyauthenticsaccharidesTOF-MSThepolymerizationwasestablishedas3AcidHydrolyzates→HPLCSaccharides1&2:Glucose,Fructose,Galactose(1:1:1)3&4:Glucose,Fructose(2:1)Methylationandmethanolysis→GLCMethylationwascarriedoutbyHakomorimethodMethanolyzedbyheatingat96℃for30minwith1.5%methanolichydrochloricacidresultExperimental1st2nd3rdHPAECTOF-saccharide31-Kestose1.101.321-Kestose1.471.06Raffinose2.633.741.453.681.29
1.082.55Methyl-1,3,4,6-tetra-O-methyl-D-fructosideMethyl-2,3,4,6-tetra-O-methyl-D-glucosideMethyl-2,3,4-tri-O-methyl-D-glucosideα-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside1.08saccharide31-Kestose1.101-KeExperimentalGlcanomericproton→H-1(δH4.98)methyleneproton→H-6(δC61.25)exhibitedcorrelationpeakstobothH-1andH-2byHMBC→C-3(δC73.8)gavecorrelationpeaktoH-1byCOSY→H-2(δH3.57)exhibitedacorrelationpeaktoH-1byHMBC→C-5(δC72.63)Theremainingmethineprotonincludedinthesamespin-spinnetworkwithH-1→H-4(δH3.44)FruThecharacteristicdoubletsignalinthe1H-NMRspectrum→H-3''(δH4.24)exhibitedacorrelationpeaktoH-3''byCOSY→H-4''(δH4.07)Themethyleneprotoninthesamespin-spinnetworkwithH-3’’,H-4’’,andH-5’’wasassigned→H-6''(δH3.86)gavecorrelationpeaktoH-4''byCOSY→H-5''(δH3.91)exhibitedacorrelationpeaktoH-3’’byHMBC→C-1''(δ62.19)Thequaternarycarbon,whichexhibitedacorrelationpeaktoH-1''byHMBC→C-2''(δ104.57)Saccharide
3ExperimentalGlcanomericprotonExperimentalYourTextHereYourTextHereThearrangementofthesugarresiduesYourTextHereTheanomericproton(H-1’)ofGlc’exhibitedacorrelationpeaktot
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