title: Synthesis of 1,4,7,10-tetra-azacyclododecan-1,4,7,10-tetra-azidoethylacetic acid (DOTAZA) and related "clickable" DOTA derivatives.
abstract: Herein, we report the synthesis of two enantiomeric DOTAZA esters and a related DOT3AZA ester. These compounds are tunable analogues of the well-known chelator DOTA and can be easily functionalized through click chemistry of the side-chain azide groups. Like DOTA, DOTAZA forms complexes with various di- and trivalent metals, as demonstrated in the synthesis and structural analysis of CuDOTAZA and the preparation of GdDOTAZA.
authors.affiliation: Department of Chemistry, Pharmaceutical and Medicinal Chemistry, University of Hamburg, Bundesstr. 45, 20146 Hamburg (Germany), Fax: (+49) 40-428383477.
authors.forename: Ella
authors.initials: E
authors.lastname: Kriemen
authors.forename: Erik
authors.initials: E
authors.lastname: Ruf
authors.forename: Ulrich
authors.initials: U
authors.lastname: Behrens
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Maison
mesh_terms: D057930:Click Chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D006573:Heterocyclic Compounds, 1-Ring; C071349:1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid
keywords: X-ray diffraction; chelates; click chemistry; coordination modes; macrocycles