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DOTAGA–Anhydride: A Valuable Building Block for the Preparation of DOTA‐Like Chelating Agents
Author(s) -
Bernhard Claire,
Moreau Mathieu,
Lhenry Damien,
Goze Christine,
Boschetti Frédéric,
Rousselin Yoann,
Brunotte François,
Denat Franck
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200132
Subject(s) - dota , acetic anhydride , chemistry , bifunctional , propylamine , chelation , combinatorial chemistry , derivative (finance) , organic chemistry , amine gas treating , financial economics , economics , catalysis
A DOTA derivative that contains an anhydride group was readily synthesized by reacting DOTAGA with acetic anhydride and its reactivity was investigated. Opening the anhydride with propylamine led to the selective formation of one of two possible regioisomers. The structure of the obtained isomer was unambiguously determined by 1D and 2D NMR experiments, including COSY, HMBC, and NOESY techniques. This bifunctional chelating agent offers a convenient and attractive approach for labeling biomolecules and, more generally, for the synthesis of a large range of DOTA derivatives. The scope of the reaction was extended to prepare DOTA‐like compounds that contained various functional groups, such as isothiocyanate, thiol, ester, and amino acid moieties. This versatile building block was also used for the synthesis of a bimodal tag for SPECT or PET/optical imaging.