Study On The Synthesis Of Novel Aromatic Boronic Acid Sensors And Fordiscimination Of Monosaccharides

Saccharide is necessary energy and physiological active substance in human body, and also plays important part in biological body. As energy storage molecule, saccharide may be oxidated to produce plenty of energy to drive metabolic processes and be transferred to protein, fat and so on. Saccharide, like amino acid and nucleotide, occupies an important position in life sciences. Therefore, the recognization of vital saccharide in life process is very important in the fields of life sciences and medical researches.In this work, three new boronic acid derivatives were synthesized. Fluorescence detection methods for the recognition of saccharide were deeply studied. The result showed that three new boronic acid derivatives for different saccharide with good recognition. This thesis consist of three parts.1. The fluorescence analytical methods for the determination of saccharide had been introduced, and the mechanisms of the fluorescence probe containing boronic acid group for saccharides recognition were summarized. The recent development of the interactions between the compound containing boronic acid group and sacchairdes was descrided further.2. Three new boronic acid derivatives , 2-[1-(2-naphthalenyl)]phenyl boronic acid(NPBA), 2-{[(5-{[2-(dihydroxyboryl)benzyl]amino}-1-naphthyl)amino]methyl phenyl boronic acid (DNBA) and 2-{[7-{[2-(dihydroxyboryl)benzyl]amino}-9H-fluoren-2-yl)amino]methyl}-phenyl boronic acid (DFBA) were synthesized. These boronic acid derivatives were purified and the structure were characterized.3. Three new boronic acid derivatives as fluorescence probe for the recognition of monosaccharides (D-Glucose, D-Fructose, D-Galactose, D-Mannose ) were studied. The binding reaction between the boronic acid derivative with saccharide including D-Glucose,D-Fructose , D-Galactose and D-Mannose was examined in 5.0×10-2 mol/L NaCl ionic buffer (60% v/v methanol in water). It is found: the fluorescence intensity of the three boronic acid derivatives were increased with the adding of saccharide; the binding reaction can be used for the identification of sugar by the chang of fluorescence intensity, and good selectivity and high sensitivity were obtained. The result showed that NPBA can be used to recognize D-Glucose with high selectivity, DNBA and DFBA can be used to recognize D-Fructose with high selectivity respectively in the four monosaccharide.The possible binding mechanism is that the intramolecular charge transfer(ICT) were used in the reaction of NPBA with saccharide ; and the photoinduced electron transfer(PET) mechanism was employed in the reaction of DNBA and DFBA with saccharide respectively . but the fluorescent increase of DFBA with D-Fructose is more stronger than DNBA with D-Fructose.Another, The linearity and limit of detection were reseached in the reaction of the three boronic acid derivatives with the four monosaccharide. The binding reaction has been applied to the determination of glucose in human plasma with satisfactory results...