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Nucleic Acids Research, 1989, Vol. 17, No. 1 285-299
© 1989

CHEMISTRY

Psoralen covalently linked to oligodeoxyribonucleotides: synthesis, sequence specific recognition of DNA and photo-cross-linking to pyrimidine residues of DNA

Uwe Pieles and Uwe Englisch

Abteilung Chemie, Max-Planck-Institut für Experimentelle Medizin Hermann-Rein-Strasse 3, 3400 Gottingen, FRG

Received August 19, 1988. Revised November 29, 1988. Accepted November 29, 1988.

The psoralen derivative 4, 5', 8-trimethylpsoralen was covalently linked to the 5'-terminus of an 18mer oligodeoxyribonucleotide in the course of solid phase synthesis using phosphoroamidite chemistry. The derivative was introduced as a phosphitylation compound in the last cycle of the oligomer synthesis. The reagent was prepared by 4'-chloromethylation of 4, 5', 8-trimethylpsoralen, introduction of a linker by ethanediol and phosphitylation with chloro-[ (ß-cyanoethoxy)-N, N-diisopropylamino ]-phosphine. After oxydation and deprotection the 5'-psoralen modified oligodeoxyribonucleotide was characterised by HPLC.

Hybridisation of the psoralen-modified oligomer to a complementary single stranded 21mer followed by irradiation at 350 nm revealed a photo-cross-linked double-stranded DNA fragment analysed on denaturing polyacrylamide gels. The cross-link could be reversed upon irradiation at 254nm.


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