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Oligonucleotides Containing Disaccharide Nucleosides
Author(s) -
Efimtseva Ekaterina V.,
Bobkov Georgii V.,
Mikhailov Sergey N.,
Van Aerschot Arthur,
Schepers Guy,
Busson Roger,
Rozenski Jef,
Herdewijn Piet
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010815)84:8<2387::aid-hlca2387>3.0.co;2-f
Subject(s) - disaccharide , chemistry , oligonucleotide , dna , stereochemistry , duplex (building) , nucleic acid , rna , nucleotide , biochemistry , gene
Disaccharide nucleosides with 2′‐ O ‐( D ‐arabinofuranosyl), 2′‐ O ‐( L ‐arabinofuranosyl), 2′‐ O ‐( D ‐ribopyranosyl), 2′‐ O ‐( D ‐erythrofuranosyl), and 2′‐ O ‐(5‐azido‐5‐deoxy‐ D ‐ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table ). Single substitution resulted in a Δ T m of +0.5 to −1.4° for DNA/RNA and a Δ T m of −0.8 to −4.7° for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH 2 −C(5″) group has a beneficial effect on duplex stability.