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Introducing structural flexibility into porphyrin–DNA zipper arrays

Introducing structural flexibility into porphyrin–DNA zipper arrays
Introducing structural flexibility into porphyrin–DNA zipper arrays
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 ?M) which is not observed by spectroscopy at lower concentrations (?1 ?M)
1477-0520
777-782
Brewer, Ashley
d10b9ab3-b920-498b-8a3c-b4b5d16106e5
Siligardi, Guiliano
1ee5bf23-843c-4d66-a455-c88f2df4db47
Neylon, Cameron
697f067b-db25-4c41-9618-28f4b74f73aa
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d
Brewer, Ashley
d10b9ab3-b920-498b-8a3c-b4b5d16106e5
Siligardi, Guiliano
1ee5bf23-843c-4d66-a455-c88f2df4db47
Neylon, Cameron
697f067b-db25-4c41-9618-28f4b74f73aa
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d

Brewer, Ashley, Siligardi, Guiliano, Neylon, Cameron and Stulz, Eugen (2011) Introducing structural flexibility into porphyrin–DNA zipper arrays. Organic & Biomolecular Chemistry, 9 (3), 777-782. (doi:10.1039/c0ob00535e).

Record type: Article

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 ?M) which is not observed by spectroscopy at lower concentrations (?1 ?M)

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Published date: 2011

Identifiers

Local EPrints ID: 176837
URI: https://eprints.soton.ac.uk/id/eprint/176837
ISSN: 1477-0520
PURE UUID: 19dea8e0-1dde-478a-8030-73bc1c2f887b
ORCID for Eugen Stulz: ORCID iD orcid.org/0000-0002-5302-2276

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Date deposited: 11 Mar 2011 11:48
Last modified: 29 Oct 2019 01:48

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