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Synthesis and Properties of Oligonucleotides Containing 2,4‐Dihydroxycyclohexyl Nucleosides
Author(s) -
Bardiot Dorothée,
Rosemeyer Helmut,
Lescrinier Eveline,
Rozenski Jef,
Van Aerschot Arthur,
Herdewijn Piet
Publication year - 2005
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/hlca.200590258
Subject(s) - chemistry , oligonucleotide , uracil , nucleic acid , stereochemistry , combinatorial chemistry , oligonucleotide synthesis , base (topology) , nucleobase , dna , biochemistry , mathematical analysis , mathematics
Cyclohexyl nucleosides with an adenine and uracil base have been synthesized from 2‐azidocyclohexane‐1,5‐diol. The obtained racemic nucleosides were resolved using ( R )‐ O ‐methylmandelic acid. Short oligonucleotides were synthesized using phorphoramidite chemistry. However, these oligonucleotides do not show self‐hybridization, and duplexes are less stable than those of ribopyranosyl‐(4′ → 2′)‐oligonucleotides.