Book of Abstracts - Ruhr-Universität Bochum

P-50
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
A Tri-organometallic Derivative Containing a PNA Backbone: Synthesis and
Antibacterial Activity
Malay Patra, a Gilles Gasser, a# Dmytro Bobukhov, b Klaus Merz, a Alexander V. Shtemenko b
Julia E. Bandow c and Nils Metzler-Nolte* a
a Lehrstuhl für Anorganische Chemie I, Fakultät für Chemie und Biochemie, Ruhr-Universität
Bochum, Gebäude NC 3 Nord, Universitätsstr. 150, 44801 Bochum, Germany; b Department of
Inorganic Chemistry, Ukrainian State Chemical Technological University, Gagarin Avenue 8,
Dnipropetrovs'k, 49005 Ukraine; c Lehrstuhl für Biologie der Mikroorganismen, Fakultät für Biologie
und Biotechnologie, Ruhr-Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany. # new
address: Institute of Inorganic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057
Zurich, Switzerland.
Novel synthetic routes for the incorporation of different organometallic entities into the same
biomolecule are highly demanded. With the strive of developing a reaction sequence for the controlled
and sequential insertion of distinct organometallics into a PNA oligomer, we have chosen, as a model
compound, namely, 2-(N-(2-(2-(9H-fluoren-9-yloxy)acetamido)ethyl)pent-4-ynamido)acetic acid
containing both a PNA backbone and an alkyne side-chain and three different organometallics,
azidomethyl ferrocene, β-cymantrenoyl-propionic acid and [{N, N-bis((pyridin-2-yl)methyl)prop-2yn-1-amine}Re(CO)3]PF6
– were inserted using click chemistry, amide bond formation and
Sonogashira coupling as orthogonal derivatisation methods respectively. Moreover, we discovered, the
triorganometallic compound (1) has excellent antibacterial activity against a number of multidrug
resistant gram-positive bacterial strains.
References
1. M. Patra, G. Gasser, D. Bobukhov, K. Merz, A.V. Shtemenko, N. Metzler-Nolte, Dalton Trans.
2010, DOI: 10.1039/c003598j.
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