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Nucleic Acids Research, 1995, Vol. 23, No. 5 788-795
© 1995

STRUCTURAL BIOLOGY

Solution structure of oligonucleotides covalently linked to a psoralen derivative

O. Bornet, C. Prévost, F. Vovelle, M. Chassignol, N.T. Thuong and G. Lancelot*

Centre de Biophysique Moleculaire, CNRS, rue Charles Sadron 45071 Orléans cédex 2, France

*To whom correspondence should be addressed

Received November 14, 1994. Revised January 20, 1995. Accepted January 20, 1995.

Psoralen (pso) was attached via its C-5 position to the 5'-phosphate group of an oligodeoxynucleotide d(TAAGCCG) by a hexamethylene linker (ms). Complex formation between pso-m6-d(TAAGCCG) and the complementary strands d(CGGCTTA)[7-7mer] or d(CGGCTTAT)[7-8mer] was Investigated by nuclear magnetic resonance in aqueous solution. Structural informations derived from DQF-COSY and NOESY maps, revealed that the mini double helix adopts a B-form conformation and that the deoxyriboses preferentially adopt a C 2'-endo conformation. The nOe connectivities observed between the protons of the bases or the sugars in each duplex, and the protons of the psoralen and the hexamethylene chain, led us to propose a model involving an equilibrium between two conformations due to different locations of the psoralen. Upon UV-irradiation, the psoralen moiety cross-linked the two DNA strands at the level of 5TpA3' sequences. NMR studies of the single major photo-cross-linked duplex pso-m6-d(TAAGCCG) and d(CGG-CTTA) were performed. The stereochemistry of the diadduct is indeed cis-syn at both cyclobutane rings. In addition, the effects of this diadduct on the helical structure are analyzed in detail.


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