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Synthesis of symmetrical, single-chain, phenylene/biphenylene-modified bolaamphiphiles

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Abstract

Two new, symmetrical, phenylene- or biphenylene-modified bolaamphiphiles bearing two phosphocholine headgroups and an alkyl spacer chain length of 32 and 36 carbon atoms, respectively, have been synthesised. The key step was the Cu(II)-catalysed Grignard reaction used either as a simultaneous bis-coupling procedure or in a stepwise homo-coupling. Particularly with the use of the homo-coupling, we were able to separate the phenylene-free by-products from the desired products. This homo-coupling additionally offered the possibility of preparing unsymmetrical bolaamphiphiles. Conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with β-bromoethylphosphoric acid dichloride and subsequent quarternisation with trimethylamine. Unlike previous studies with aliphatic bolaamphiphiles that formed flexible nanofibres in aqueous suspension, the bolaamphiphiles of the present study, containing phenylene- and biphenylene groups in the middle part of the alkyl spacer chain, formed small ellipsoidal aggregates at ambient temperature.

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Acknowledgments

This work was supported by grants from the Deutsche Forschungsgemeinschaft (projects Bl 182/19-3 and Do 463/4-2). We thank Prof. Andrea Sinz and Dr. Christian Ihling (Department of Pharmaceutical Chemistry and Bioanalytics, Martin-Luther-University Halle-Wittenberg) for the high resolution mass spectrometry analysis. The support of Dr. Gerd Hause (Biocenter, Martin-Luther-University Halle-Wittenberg) by providing us access to the electron microscope facility is greatly appreciated. Finally, S.D. and B.D. thank Dipl.-Pharm. Susann Althaus and Dr. Beate Stiebitz for the help in the synthesis.

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Authors and Affiliations

  1. Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120, Halle (Saale), Germany

    Simon Drescher, Stefan Sonnenberger & Bodo Dobner

  2. Institute of Chemistry, Martin-Luther-University Halle-Wittenberg, von-Danckelmann-Platz 4, 06120, Halle (Saale), Germany

    Annette Meister & Alfred Blume

Authors
  1. Simon Drescher
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  2. Stefan Sonnenberger
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  3. Annette Meister
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  4. Alfred Blume
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  5. Bodo Dobner
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Correspondence to Simon Drescher.

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Drescher, S., Sonnenberger, S., Meister, A. et al. Synthesis of symmetrical, single-chain, phenylene/biphenylene-modified bolaamphiphiles. Monatsh Chem 143, 1533–1543 (2012). https://doi.org/10.1007/s00706-012-0833-2

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  • DOI: https://doi.org/10.1007/s00706-012-0833-2

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