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Issue 3, 2011
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Introducing structural flexibility into porphyrin–DNA zipper arrays

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Abstract

A more flexible nucleotide building block for the synthesis of new DNA based porphyrin–zipper arrays is described. Changing the rigid acetylene linker between the porphyrin substituent and the 2′-deoxyuridine to a more flexible propargyl amide containing linkage leads in part to an increased duplex stability. The CD spectra reveal different electronic interactions between the porphyrins depending on the type of linker used. Molecular modelling suggests large variation of the relative orientation of the porphyrins within the major groove of the DNA. The porphyrins can be metallated post-synthetically with different metals as shown with zinc, cobalt and copper. The spectroscopic features do not alter drastically upon metallation apart from the CD spectra, and the stability of the metal complex is highly dependent on the nature of the metal. As shown by CD spectroscopy, the zinc porphyrin is rapidly demetallated at high temperatures. Globular structure determination using SAXS indicates that a molecular assembly comprised of a two to four helical bundle dominates in solution at higher concentrations (≥50 μM) which is not observed by spectroscopy at lower concentrations (≤1 μM).

Graphical abstract: Introducing structural flexibility into porphyrin–DNA zipper arrays

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The article was received on 04 Aug 2010, accepted on 12 Oct 2010 and first published on 13 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00535E
Citation: Org. Biomol. Chem., 2011,9, 777-782
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    Introducing structural flexibility into porphyrin–DNA zipper arrays

    A. Brewer, G. Siligardi, C. Neylon and E. Stulz, Org. Biomol. Chem., 2011, 9, 777
    DOI: 10.1039/C0OB00535E

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