Modification of agarose: 6-Aminoagarose mediated syntheses of fluorogenic pyridine carboxylic acid amides

• Published in: Carbohydrate polymers Vol. 106; pp. 365 - 373
• Main Authors: KONDAVEETI, Stalin, MEHTA, Gaurav K, SIDDHANTA, A. K
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier 15.06.2014
• Subjects: Amides - chemical synthesis; Amino Sugars - chemistry; Applied sciences; Azo Compounds - chemistry; Carbohydrate Conformation; Carboxylic Acids - chemistry; Cross-Linking Reagents - chemistry; Exact sciences and technology; Fluorescent Dyes - chemical synthesis; Hydrogels; Iridoids - chemistry; Microwaves; Natural polymers; Niacin - chemistry; Nuclear Magnetic Resonance, Biomolecular; Organophosphorus Compounds; Phthalimides - chemistry; Physicochemistry of polymers; Picolinic Acids - chemistry; Pyridines - chemical synthesis; Sepharose - analogs & derivatives; Sepharose - chemistry; Solutions; Spectrophotometry; Spectroscopy, Fourier Transform Infrared; Starch and polysaccharides; Pyridine derivative polymer; Molecular structure; Nicotinic acid; Fluorescence; Experimental study; Emission spectrum; Agarose; Amidation; Picolinic acid; Chemical modification; Amination; Fluorescent material; Amine polymer; Gel point; Preparation; Optical activity; Microwave irradiation; Oside polymer; Amide; Aqueous solution; Hydrogel; Aminoagarose
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2014.02.051

A facile 6-aminoagarose (AA) mediated synthesis of new fluorogenic amides of agarose with nicotinic (AA-NA) and picolinic acids (AA-PA) employing carbodiimide chemistry have been described. 6-Amino agarose (AA) was synthesized in a facile Mitsunobu-inspired microwave mediated method involving the reaction of agarose with phthalimide in presence of diisopropyl azodicarboxylate and triphenylphosphene (DIAD/TPP) followed by hydrazinolysis. All compounds were characterized by GPC, UV spectrophotometry, fluorescence spectroscopy, FT-IR, (1)H and (13)C NMR spectra. The fluorescence emissions (λmax 430 and 412 nm) of 1 × 10(-3)M solutions of AA-NA and AA-PA in water were significantly higher (ca. 82% and ca. 90%) than those of the molar equivalents (0.2mg) of NA and PA present in the 1 × 10(-3)M solutions of the amides, respectively. These fluorogenic pyridine carboxylic acid amides of agarose may find applications as sensors in biomedical and pharmaceutical industries.