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Efficient Synthesis of 1,4,7‐Triazacyclononane and 1,4,7‐Triazacyclononane‐Based Bifunctional Chelators for Bioconjugation
Author(s) -
Désogère Pauline,
Rousselin Yoann,
Poty Sophie,
Bernhard Claire,
Goze Christine,
Boschetti Frédéric,
Denat Franck
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402708
Subject(s) - aminal , bioconjugation , chemistry , bifunctional , diethylenetriamine , combinatorial chemistry , chelation , catalysis , organic chemistry
The reaction of diethylenetriamine with chloroacetaldehyde yielded a bicyclic aminal intermediate for the synthesis of 1,4,7‐triazacyclononane (TACN), a macrocyclic polyamine the derivatives of which find applications as catalysts, bleaching agents, and chelators for medical imaging. This new synthetic protocol outperforms the synthetic methods described so far because it does not involve any cyclization step. Moreover, this aminal intermediate allowed access to a new family of TACN derivatives functionalized on the carbon skeleton, for example, C ‐aminomethyl‐TACN. This novel compound is a precursor of valuable bifunctional chelating agents for nuclear medicine, in particular, for the preparation of PET imaging agents after bioconjugation and metallation with 68 Ga or 64 Cu.