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

Melanie Schmidlehner, Felix Faschinger, Lorenz Reith, Martin Ertl, Wolfgang Schöfberger

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, novel water-​sol. corrole amino acid conjugates were synthesized and characterized. The coupling reaction of A2B- and A3-​corroles with glycine Et 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) A3-​corrole towards O2 evolution. First we employed tert-​Bu hydroperoxide (t-​BuOOH) as oxidant to obtain the Mn(V)​oxo species and tetra-​Bu ammonium hydroxide (TBAH) as hydroxide donor agent. Furthermore, the binding properties of the non-​metalated and the Mn(III) A3-​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) A3-​corrole​/amino sulfonic acid deriv. was synthesized and we briefly describe the photophys. properties of this compd.
Original languageEnglish
Pages (from-to)395-405
Number of pages11
JournalApplied Organometallic Chemistry
Volume27
Issue number7
DOIs
Publication statusPublished - 2013

Fields of science

  • 103 Physics, Astronomy
  • 104003 Inorganic chemistry
  • 104 Chemistry
  • 107 Other Natural Sciences
  • 301904 Cancer research
  • 301305 Medical chemistry

JKU Focus areas

  • Nano-, Bio- and Polymer-Systems: From Structure to Function
  • Engineering and Natural Sciences (in general)

Cite this