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Synthesis and Spectroscopic Properties of Porphyrin-Substituted Uridine and Deoxyuridine

Synthesis and Spectroscopic Properties of Porphyrin-Substituted Uridine and Deoxyuridine
Synthesis and Spectroscopic Properties of Porphyrin-Substituted Uridine and Deoxyuridine
A general synthetic route to porphyrin-substituted uridine and 2'-deoxyuridine using Sonogashira coupling with acetylene porphyrins is presented. Both diphenyl and tetraphenyl porphyrins, as free base or zinc metallated, can be attached to the nucleobase. Selective TBDMS protection of the deoxyribose does not affect the coupling reaction. The substituents on the porphyrins render the conjugates soluble either in organic solvents (carboxy esters) or in water (carboxylates). No electronic communication between the chromophore and the nucleobase occurs, as indicated by UV/Vis spectroscopy. In aqueous solution, the absorption of the porphyrins is substantially lower than in organic solvents.
porphyrins, nucleosides, cross-coupling, spectroscopy, protecting groups
0936-5214
1579-1583
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 (2004) Synthesis and Spectroscopic Properties of Porphyrin-Substituted Uridine and Deoxyuridine. Synlett, (9), 1579-1583. (doi:10.1055/s-2004-829541).

Record type: Article

Abstract

A general synthetic route to porphyrin-substituted uridine and 2'-deoxyuridine using Sonogashira coupling with acetylene porphyrins is presented. Both diphenyl and tetraphenyl porphyrins, as free base or zinc metallated, can be attached to the nucleobase. Selective TBDMS protection of the deoxyribose does not affect the coupling reaction. The substituents on the porphyrins render the conjugates soluble either in organic solvents (carboxy esters) or in water (carboxylates). No electronic communication between the chromophore and the nucleobase occurs, as indicated by UV/Vis spectroscopy. In aqueous solution, the absorption of the porphyrins is substantially lower than in organic solvents.

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More information

Published date: 2004
Keywords: porphyrins, nucleosides, cross-coupling, spectroscopy, protecting groups

Identifiers

Local EPrints ID: 41345
URI: https://eprints.soton.ac.uk/id/eprint/41345
ISSN: 0936-5214
PURE UUID: a3ee1f8f-0e43-412f-84cb-744680272f9b
ORCID for Eugen Stulz: ORCID iD orcid.org/0000-0002-5302-2276

Catalogue record

Date deposited: 23 Aug 2006
Last modified: 18 Jul 2019 12:25

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