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Bioconjugates of enantiomerically pure organopalladium compounds by metal-assisted positional selective transesterifications at palladium enolates

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The synthesis of enantiomerically pure palladatricyclo[4.1.0.02,4]heptanes and their modification by an unprecedented and very efficient positional selective transesterification is described. The mild reaction conditions are most probably based on an acceleration of the transesterification due to as...

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Main Authors: Hashmi, A. Stephen K. (Author) , Riedel, Dominic (Author) , Grundl, Marc A. (Author) , Wittel, Bärbel C. (Author) , Föll, Andreas (Author) , Lubkoll, Jana (Author) , Traut, Telisha (Author) , Hewer, Raymond (Author) , Rominger, Frank (Author) , Frey, Wolfgang (Author) , Bats, Jan W. (Author)
Format: Article (Journal)
Language:English
Published: 21 April 2011
In: Chemistry - a European journal
Year: 2011, Volume: 17, Issue: 23, Pages: 6407-6414
ISSN:1521-3765
DOI:10.1002/chem.201003308
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201003308
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201003308
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Author Notes:A. Stephen K. Hashmi, Dominic Riedel, Marc A. Grundl, Bärbel C. Wittel, Andreas Föll, Jana Lubkoll, Telisha Traut, Raymond Hewer, Frank Rominger, Wolfgang Frey, and Jan W. Bats
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Summary:The synthesis of enantiomerically pure palladatricyclo[4.1.0.02,4]heptanes and their modification by an unprecedented and very efficient positional selective transesterification is described. The mild reaction conditions are most probably based on an acceleration of the transesterification due to assistance by the metal. This novel approach allows straightforward access to a large number of structurally diverse organometallic complexes. The functional groups on the newly installed ester moieties were modified by using standard peptide synthesis protocols, Sonogashira reactions, and nucleophilic substitution reactions. The cellular uptake of these organometallic species was traced by confocal microscopy and their biological activity was evaluated by using different cell lines. Inhibition of cell growth and induction of apoptotic cell death by these novel palladium heterocycles are equivalent to Cisplatin.
Item Description:Gesehen am 07.09.2022
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201003308

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