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Water‐soluble metalated and non‐metalated A 2 B‐ and A 3 ‐corrole/amino acid conjugates: syntheses, characterization and properties
Author(s) -
Schmidlehner Melanie,
Faschinger Felix,
Reith Lorenz Michael,
Ertl Martin,
Schoefberger Wolfgang
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2992
Subject(s) - corrole , chemistry , ammonium hydroxide , amino acid , sulfonic acid , metalation , conjugate , hydroxide , tetrabutylammonium hydroxide , conjugate acid , combinatorial chemistry , glycine , organic chemistry , biochemistry , ion , mathematical analysis , mathematics
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 © 2013 John Wiley & Sons, Ltd.