Book of Abstracts - Ruhr-Universität Bochum

P-67
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
Synthesis of Mixed Gold(I)-Phosphine-Ferrocene-Phenylalanine
and Peptide Conjugates
Christine Doffek, a S. David Köster, a and Nils Metzler-Nolte *a
a Ruhr-Universität Bochum, Lehrstuhl für Anorganische Chemie I, Universitätsstraße 150,
D-44801 Bochum, Germany. E-mail: christine.doffek@rub.de
The combination of gold(I)-phosphine and ferrocene derivatives enlarges the number of interesting
bioconjugates. The gold(I)-phosphine-ferrocene-phenylalanine conjugate 1 was prepared by Cu(I)catalyzed
[3+2]-cycloaddition of azido-modified phenylalaninemethylester with the internal alkyne of
a gold(I)-phosphine-ferrocene-acetylide in good yields. 1,2 The corresponding peptide conjugate was
synthesized using solid phase peptide synthesis (SPPS) in combination with Cu(I)-catalyzed [3+2]cycloaddition
of the azido-modified peptide with the gold(I)-phosphine-ferrocene-acetylide, also
showing good yields. During the final cleavage the peptide conjugate decomposed. The gold(I)phosphine-ferrocene-phenylalanine
conjugate 1 was comprehensively characterized by multinuclear
and multidimensional NMR spectroscopy, mass spectrometry and cyclic voltammetry (CV). The
electrochemical studies showed reversible processes of the redox couple Fc 0 /Fc + (Fc = ferrocenyl) and
an irreversible reduction of Au + to Au 0 .
References
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O
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1
Au
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1. D. A. Gray, L. Gao, T. S. Teets, J. B. Updegraff III, N. Deligonul, T. G. Gray, Organometallics
2009, 28, 6171-6182.
2. S. Back, R. A.. Gossage, H. Lang, G. van Koten, Eur. J. Inorg. Chem. 2000, 1457-1464.
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