title: Aminoalkyl functionalization of dextran for coupling of bioactive molecules and nanostructure formation.
abstract: Aminopropyl dextrans and mixed aminopropyl cyanoethyl dextrans were prepared from cyanoethyl precursors by full or partial reduction with CoCl2/NaBH4. Coupling of various aldehydes to the glucan backbone by reductive amination was accomplished with 4-hydroxy-3-methoxybenzaldehyde (vanillin), 3,5-di-tert-butyl-4-hydroxy-benzaldehyde (BHT-CHO), maltose and maltotriose, and picoline borane as reducing agent. Successful coupling of these representatives for aroma compounds, antioxidants and sugar side-chains were verified by ESI-MS after hydrolysis and by 1D and 2D NMR spectroscopy. Degree of conversion (molar ratio of coupled aldehydes) was estimated from (1)H NMR spectra. Formation of secondary and tertiary amines was detectd by ESI-MS. Applying a solvent exchange process, new nanoparticles based on these modified dextrans were prepared with and without addition of iron oxide nanoparticles.
authors.affiliation: Institute for Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, D-38106 Braunschweig, Germany.
authors.forename: Kathrin
authors.initials: K
authors.lastname: Fiege
authors.forename: Heinrich
authors.initials: H
authors.lastname: Lünsdorf
authors.forename: Petra
authors.initials: P
authors.lastname: Mischnick
mesh_terms: D000586:Amination; D001547:Benzaldehydes / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D002084:Butylated Hydroxytoluene / Q000031:analogs & derivatives / Q000737:chemistry; D003911:Dextrans / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry; D008320:Maltose / Q000737:chemistry; D046529:Microscopy, Electron, Transmission; D049329:Nanostructures / Q000737:chemistry* / Q000648:ultrastructure; D021241:Spectrometry, Mass, Electrospray Ionization; D014312:Trisaccharides / Q000737:chemistry
chemical_list: D001547:Benzaldehydes; D001880:Boranes; D003911:Dextrans; D005290:Ferric Compounds; D014312:Trisaccharides; C000499:ferric oxide; D002084:Butylated Hydroxytoluene; C008317:maltotriose; D008320:Maltose; C513957:3,5-di-tert-butyl-4-hydroxybenzaldehyde; C100058:vanillin