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Porphyrin substituted Dinucleotides: Synthesis and Spectroscopy

Porphyrin substituted Dinucleotides: Synthesis and Spectroscopy
Porphyrin substituted Dinucleotides: Synthesis and Spectroscopy
Deoxyuridine, which is substituted with either 5,15-diphenyl porphyrin (DPP) or 5,10,15,20-tetraphenyl porphyrin (TPP) at the 5-position via an alkynyl linker, was dimerised to the homo- and hetero-porphyrin dinucleotide. The synthesis was performed either in solution or on solid phase in order to compare the reactivity of the phosphoramidite building blocks under both conditions. The absorbance properties reveal electronic interactions in the dimers that are strongly dependent on the nature of the porphyrin. The DPP-containing dimers show significant differences between the calculated and the measured UV-Vis spectra, whereas in the TPP dimer hardly any difference is observed. Formation of the duplex with the corresponding diadenosine changes the electronic interactions between the chromophores in the heteroporphyrin dimer, as shown by a blue shift of the absorbance. The low solubility of the DPP dimer in pure chloroform prevented formation of the duplex due to the necessity to add about 10% of methanol. The dimerisation is detectable using MALDI-TOF mass spectrometry for all dinucleotides.
Dinucleotide · MALDI-TOF MS · Modified nucleotide · Porphyrin · Spectroscopy
101-104
Bouamaied, Imenne
9938a8f5-740f-4c9c-9285-8a16a43a5fe5
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d
Bouamaied, Imenne
9938a8f5-740f-4c9c-9285-8a16a43a5fe5
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d

Bouamaied, Imenne and Stulz, Eugen (2005) Porphyrin substituted Dinucleotides: Synthesis and Spectroscopy. Chimia, 59 (3), 101-104.

Record type: Article

Abstract

Deoxyuridine, which is substituted with either 5,15-diphenyl porphyrin (DPP) or 5,10,15,20-tetraphenyl porphyrin (TPP) at the 5-position via an alkynyl linker, was dimerised to the homo- and hetero-porphyrin dinucleotide. The synthesis was performed either in solution or on solid phase in order to compare the reactivity of the phosphoramidite building blocks under both conditions. The absorbance properties reveal electronic interactions in the dimers that are strongly dependent on the nature of the porphyrin. The DPP-containing dimers show significant differences between the calculated and the measured UV-Vis spectra, whereas in the TPP dimer hardly any difference is observed. Formation of the duplex with the corresponding diadenosine changes the electronic interactions between the chromophores in the heteroporphyrin dimer, as shown by a blue shift of the absorbance. The low solubility of the DPP dimer in pure chloroform prevented formation of the duplex due to the necessity to add about 10% of methanol. The dimerisation is detectable using MALDI-TOF mass spectrometry for all dinucleotides.

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More information

Published date: 2005
Keywords: Dinucleotide · MALDI-TOF MS · Modified nucleotide · Porphyrin · Spectroscopy

Identifiers

Local EPrints ID: 41347
URI: https://eprints.soton.ac.uk/id/eprint/41347
PURE UUID: 68ad31ff-dec6-4199-a9e1-5b6df17049b6
ORCID for Eugen Stulz: ORCID iD orcid.org/0000-0002-5302-2276

Catalogue record

Date deposited: 22 Aug 2006
Last modified: 06 Jun 2018 12:40

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