Synthesis And Properties Of Iduronic Acid,Industrial Oil And Fluorescent Probes Based On Monosaccharides

In this thesis,monosaccharides were used to synthesize the methyl-1,2,3-tri-O-acetyl-4-O-benzyl-L-idopyranuronate,the target compounds for textile industry oil,the sugar based fluorescent probe for detection of ?-galactosidase and another probe for detection of glutathione(GSH).The main research contents of the thesis are listed as follows:Starting from D-glucose,methyl-1,2,3-tri-O-acetyl-4-O-benzyl-L-idopyranuronate was obtained by nine steps reaction such as protection,deprotection,oxidation by Tempoand methylation,configuration reversal of C-5-hydroxyl,and acetylation successively.Then we studied the effects of reaction temperature,catalyst,reaction material ratio on the yield.The total yield was 25%?Methyl keto-?-glucoside was synthesized by the Knoevenagel condensation reaction with D-glucose as the raw material.The methyl keto-?-glucoside stearate was synthesized under the catalysis of sodium hydroxide.The optimum reaction condition is n(Methyl keto-?-glucoside):n(stearic acid)= 1:1.36,reaction temperature:135?,catalyst dosage:2%,reaction time:8 h.Finally,the surface tension,foam stability,hydrophile lipophilic balance(HLB)value andcritical micell concentration(CMC)value were tested.Starting from D-galactose,a novel fluorescent probe was synthesized based on dicyanoisophorone(DCI)backbone as a fluorophore.Upon the addition of ?-gal,DCI-Pgal showed fluorescence enhancement within 45 min by 30 fold with a large Stokes shift of 136 nm.The probe was also used to quantify ?-gal with the detection limit as low as 3.3×10-3 U/mL.The probe exhibited a high sensitivity for ?-gal,which was further research in cellular imaging for endogenous ?-gal in OVCAR-3 cells with low cytotoxicity.Additionally,another new fluorescent probe(DCI-S)which was also based on dicyanoisophorone(DCI)backbone as a fluorophore,has been designed and synthesized toward GSH.The spectral changes exhibited that DCI-S showed an excellent selectivity and sensitivity toward GSHwith the detection limit as low as 0.33?M in 50 min.