Water-soluble metalated and non-metalated A2B- and A3-corrole/amino acid conjugates: syntheses, characterization and properties

In this study, novel water-soluble corrole amino acid conjugates were synthesized and characterized. The coupling reaction of A(2)B- and A(3)-corroles with glycine ethyl ester and taurine under strong basic conditions proved to be successful and yielded di- and trifunctionalized corrole amino acid conjugates in good yields. The subsequent metalation of the corrole/amino acid conjugates broadens the scope for applications considerably. As examples, we herein show the catalytic activity of the Mn(III) A(3)-corrole towards O-2 evolution. First we employed tert-butyl hydroperoxide (t-BuOOH) as oxidant to obtain the Mn(V)oxo species and tetrabutyl ammonium hydroxide (TBAH) as hydroxide donor agent. Furthermore, the binding properties of the non-metalated and the Mn(III) A(3)-corrole/amino sulfonic acid conjugates and transport of proteins were investigated and the conjugates exhibited binding to human serum albumin (HSA). Finally, a novel Ga(III) A(3)-corrole/amino sulfonic acid derivative was synthesized and we briefly describe the photophysical properties of this compound. Copyright (C) 2013 John Wiley & Sons, Ltd.