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Nucleic Acids Research, 1992, Vol. 20, No. 18 4711-4716
© 1992

CHEMISTRY

Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability

Koen Augustyns, Frank Vandendriessche, Arthur Van Aerschot, Roger Busson, Claus Urbanke1 and Piet Herdewijn*

Laboratory of Pharmaceutical Chemistry, Rega Institute for Medical Research Minderbroedersstraat 10, B-3000 Leuven 1Medizinische Hochschule Konstanty Gutschow Straße 8, 3000 Hannover, Germany

*To whom correspondence should be addressed

Received July 30, 1992. Accepted August 24, 1992.

Oligonucleotides containing 1-(2,4-dideoxy-ß-D-erythro-hexo-pyranosyl)thymine (2) and 1-{3,4-dideoxy-ß-De-erythro-hexopyranosyl) thymine (3) were synthesized on a solid support using the phosphoramldite approach. The properties of these oligonucleotides were compared with the earlier reported characteristics of oligonucleotides containing 1-(2,3-dideoxy-ß-De-erythro-hexopyranosyl) thymine (1). The order in enzymatic stability of end-substituted oligonucleotides is 3>1>>2 . The hybridization properties of the modified oligonucleotides are in reverse order: 2>>1>3.


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