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Open Access Porphyrin-Substituted Dinucleotides: Synthesis and Spectroscopy

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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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Keywords: DINUCLEOTIDE; MALDI-TOF MS; MODIFIED NUCLEOTIDE; PORPHYRIN; SPECTROSCOPY

Document Type: Research Article

Publication date: March 1, 2005

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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