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Nucleic Acids Research, Vol 26, Issue 4 1010-1018, Copyright © 1998 by Oxford University Press

ARTICLES

1-Deazaadenosine: synthesis and activity of base-modified hammerhead ribozymes

F Seela, H Debelak, N Usman, A Burgin and L Beigelman
Laboratorium fur Organische und Bioorganische Chemie, Institut fur Chemie, Universitat Osnabruck, Barbarastrasse 7, D-49069 Osnabruck, Germany. fraseela@rz.uni-osnabrueck.de

The incorporation of 1-deazaadenosine (c1A, 1b) into a hammerhead ribozyme and the resulting catalytic activity is described. For this purpose the phosphoramidite 2a and the 3'-phosphonate 2b as well as Fractosil-linked 1-deazaadenosine (3b) were prepared. The methoxyacetyl group was used for the 6-amino group protection and the triisopropylsilyl residue was introduced as the 2'-OH protecting group. Replacement of residues A14and A15.1 of the hammerhead ribozyme by 1- deazaadenosine resulted in a significantly reduced catalytic activity. Substitution of the A6, A9 and A13 residues has only a minor influence. The findings observed on ribozymes modified with 1-deazaadenosine were compared with those containing other adenosine analogues.
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