Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: Synthesis, hybridization and antisense properties

Article abstract of DOI:10.1080/15257770008045466

Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine (7, ara-A^2′F) and -guanine (12, ara-G^2′F) was accomplished via the condensation of 2,6-dichloropurine (1) with 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (2) as a key chemical step. Condensation of silylated N⁶-benzoyladenine (6) with 2 gave, after deblocking and chromatographic separation, ara-A^2′F (7) (14%), it's α-anomer 8 (14%) and N⁷-α-isomer 9 (25%). The PSEUROT analysis of N⁹-β-D-arabinosides 7 and 12 manifested slight preference for the S rotamer (64%) for the former, and an equal population of the N and S rotamers for the latter. The arabinosides 7 and 12 were used for the preparation of the respective phosphoamidite building blocks 13 and 14 for automated oligonucleotide synthesis. Four 15-mer oligonucleotides (ONs) complementary to the initiation codon region of firefly luciferase mRNA were prepared: unmodified 2′-deoxy-ON (AS 1) and containing (i) ara-A^2′F instead of the only A (AS2), (ii) ara-G^2′F vs. 3-G from the 5′-terminus (AS3), and (iii) both arabinosides at the same positions (AS4). All these ONs display practically the same (i) affinity to both complementary DNA and RNA, and (ii) ability to inhibit a luciferase gene expression in a cell-free transcription-translation system.

Full text of DOI:10.1080/15257770008045466

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Oligonucleotides Containing 9-(2-
Deoxy-2-Fluoro-β-D-Arabinofuranosyl)-
Adenine and -Guanine: Synthesis,
Hybridization and Antisense Properties
Tuula Tennilä a , Elena Azhayeva a , Jouko Vepsäläinen b , Reino
Laatikainen b , Alex Azhayev a & Igor A. Mikhailopulo c
a Departments of Pharmaceutical Chemistry, University of Kuopio,
P.O. Box 1627, FIN-70211, Kuopio, Finland
b Departments of Chemistry, University of Kuopio, P.O. Box 1627,
FIN-70211, Kuopio, Finland
c Departments of Institute of Bioorganic Chemistry, National
Academy of Sciences, 220141 Minsk, Acad. Kuprevicha 5, Belarus
Available online: 17 Apr 2008
To cite this article: Tuula Tennilä, Elena Azhayeva, Jouko Vepsäläinen, Reino Laatikainen, Alex
Azhayev & Igor A. Mikhailopulo (2000): Oligonucleotides Containing 9-(2-Deoxy-2-Fluoro-β-D-
Arabinofuranosyl)-Adenine and -Guanine: Synthesis, Hybridization and Antisense Properties,
Nucleosides, Nucleotides and Nucleic Acids, 19:10-12, 1861-1884
To link to this article: http://dx.doi.org/10.1080/15257770008045466
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