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Nucleic Acids Research, Vol 25, Issue 15 3034-3041, Copyright © 1997 by Oxford University Press

ARTICLES

Synthesis and hybridization properties of inverse oligonucleotides

M Marangoni, A Van Aerschot, P Augustyns, J Rozenski and P Herdewijn
Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium.

The synthesis of adenine and thymine cyclopentylethyl nucleosides is presented. This novel constrained monomeric building block is very difficult to incorporate into oligonucleotides. It was introduced in 13mer oligodeoxynucleotide sequences at a single position using H- phosphonate chemistry. Phosphoramidite chemistry completely failed in this particular case. The H-phosphonate building blocks were obtained starting from the corresponding phosphoramidites. Stability of duplexes with RNA and DNA is significantly reduced.
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Z. Lei, L. Zhang, L. R. Zhang, J. Chen, J. M. Min, and L. H. Zhang
Hybrid characteristics of oligonucleotides consisting of isonucleoside 2',5'-anhydro-3'-deoxy-3'-(thymin-1-yl)-D-mannitol with different linkage modes
Nucleic Acids Res., April 1, 2001; 29(7): 1470 - 1475.
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