title: Synthesis of water-compatible imprinted polymers of in situ produced fructosazine and 2,5-deoxyfructosazine.
abstract: Fructosazine and 2,5-deoxyfructosazine are two natural chemicals with various applications as flavoring agents in food and tobacco industry; the 2,5-deoxyfructosazine has also anti-diabetic and anti-inflammatory activities. In order to quantify these compounds in natural samples such as plant or food, we have developed a selective technique based on a water-compatible molecularly imprinted polymer (MIP). MIPs are prepared with a covalent approach from 2,5-deoxyfructosazine as template formed in situ by the self-condensation of glucosamine with vinylphenyl boronic acid, taken as catalyst and covalent monomer during the pre-complexation step. Acrylamide and polyethylene glycol diacrylate are used as supplementary non-covalent functional monomer and cross-linker, respectively. For the first time, a highly cross-linked but highly polar imprinted polymer of fructosazine and deoxyfructosazine is obtained as a solid material and not a gel. Amount of monomers is optimized to obtain high selectivity for both molecules. Results show that the MIPs prepared have a significant imprinting effect with a resulting imprinting factor of 3 for both templates. Molecularly imprinted solid-phase extraction is then performed and could be used in routine analysis to extract 2,5-deoxyfructosazine and fructosazine from soy sauce.
authors.affiliation: Institut de Chimie Organique et Analytique-UMR CNRS 7311, Université d'Orléans, 45067 Orléans, France.
authors.forename: Nathaly
authors.initials: N
authors.lastname: Henry
authors.forename: Raphaël
authors.initials: R
authors.lastname: Delépée
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Seigneuret
authors.forename: Luigi A
authors.initials: LA
authors.lastname: Agrofoglio
mesh_terms: D000327:Adsorption; D001897:Boronic Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005944:Glucosamine / Q000737:chemistry; D055772:Green Chemistry Technology; D008958:Models, Molecular; D008968:Molecular Conformation; D054802:Molecular Imprinting; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*; D011719:Pyrazines / Q000737:chemistry* / Q000302:isolation & purification; D052616:Solid Phase Extraction; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D045730:Soy Foods / Q000032:analysis; D014753:Vinyl Compounds / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: C427523:4-vinylphenyl boronic acid; D001897:Boronic Acids; D011108:Polymers; D011719:Pyrazines; D012997:Solvents; D014753:Vinyl Compounds; D014867:Water; C017737:tagatosazine; C069873:deoxyfructosazine; D005944:Glucosamine