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Book of Abstracts - Ruhr-Universität Bochum

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P-67<br />

ISBOMC `10 5.7 – 9.7. 2010 <strong>Ruhr</strong>-<strong>Universität</strong> <strong>Bochum</strong><br />

Synthesis <strong>of</strong> Mixed Gold(I)-Phosphine-Ferrocene-Phenylalanine<br />

and Peptide Conjugates<br />

Christine D<strong>of</strong>fek, a S. David Köster, a and Nils Metzler-Nolte *a<br />

a <strong>Ruhr</strong>-<strong>Universität</strong> <strong>Bochum</strong>, Lehrstuhl für Anorganische Chemie I, <strong>Universität</strong>sstraße 150,<br />

D-44801 <strong>Bochum</strong>, Germany. E-mail: christine.d<strong>of</strong>fek@rub.de<br />

The combination <strong>of</strong> gold(I)-phosphine and ferrocene derivatives enlarges the number <strong>of</strong> interesting<br />

bioconjugates. The gold(I)-phosphine-ferrocene-phenylalanine conjugate 1 was prepared by Cu(I)catalyzed<br />

[3+2]-cycloaddition <strong>of</strong> azido-modified phenylalaninemethylester with the internal alkyne <strong>of</strong><br />

a gold(I)-phosphine-ferrocene-acetylide in good yields. 1,2 The corresponding peptide conjugate was<br />

synthesized using solid phase peptide synthesis (SPPS) in combination with Cu(I)-catalyzed [3+2]cycloaddition<br />

<strong>of</strong> the azido-modified peptide with the gold(I)-phosphine-ferrocene-acetylide, also<br />

showing good yields. During the final cleavage the peptide conjugate decomposed. The gold(I)phosphine-ferrocene-phenylalanine<br />

conjugate 1 was comprehensively characterized by multinuclear<br />

and multidimensional NMR spectroscopy, mass spectrometry and cyclic voltammetry (CV). The<br />

electrochemical studies showed reversible processes <strong>of</strong> the redox couple Fc 0 /Fc + (Fc = ferrocenyl) and<br />

an irreversible reduction <strong>of</strong> Au + to Au 0 .<br />

References<br />

O<br />

O<br />

O<br />

125<br />

1<br />

Au<br />

N<br />

N<br />

N<br />

1. D. A. Gray, L. Gao, T. S. Teets, J. B. Updegraff III, N. Deligonul, T. G. Gray, Organometallics<br />

2009, 28, 6171-6182.<br />

2. S. Back, R. A.. Gossage, H. Lang, G. van Koten, Eur. J. Inorg. Chem. 2000, 1457-1464.<br />

Fe

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