title: Hyaluronic acid derivatives prepared in aqueous media by triazine-activated amidation.
abstract: A method is presented for the preparation of hyaluronic acid derivatives obtained through triazine-activated amidation. A number of amines were successfully reacted with hyaluronic acid carboxyl groups using 2-chloro-4,6-dimethoxy-1,3,5-triazine as an activating species in a mixture of water and acetonitrile under neutral conditions. By varying the amount of triazine reagent, it was possible to control the degree of modification. Depending on the amine chosen, degrees of modification ranging from 3 to 20% were obtained when using 0.5 equiv of the triazine to hyaluronic acid carboxyl groups. The possibility to perform the reaction in a mixture of water and acetonitrile facilitates the introduction of a wide range of both hydrophilic and hydrophobic amines. Triazine-activated amidation appears to be a highly versatile, controllable, and relatively mild technique for modification of hyaluronic acid, and we predict that it will be useful in the design of novel hyaluronic acid based biomaterials.
authors.affiliation: Polymer Chemistry, Department of Materials Chemistry, Uppsala University, Uppsala, Sweden. bergman@polymer.uu.se
authors.forename: Kristoffer
authors.initials: K
authors.lastname: Bergman
authors.forename: Christer
authors.initials: C
authors.lastname: Elvingson
authors.forename: Jöns
authors.initials: J
authors.lastname: Hilborn
authors.forename: Göran
authors.initials: G
authors.lastname: Svensk
authors.forename: Tim
authors.initials: T
authors.lastname: Bowden
mesh_terms: D000577:Amides / Q000737:chemistry*; D006820:Hyaluronic Acid / Q000737:chemistry*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D012542:Scattering, Radiation; D013050:Spectrometry, Fluorescence; D014227:Triazines / Q000737:chemistry*
chemical_list: D000577:Amides; D014227:Triazines; D006820:Hyaluronic Acid