173776-12-0Relevant articles and documents
1-(2-Deoxy-α- and β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane Derivatives as Conformational Probes for altDNA Oligonucleotides
Scremin, Carlo L.,Boal, Jila H.,Wilk, Andrzej,Phillips, Lawrence R.,Zhou, Liang,Beaucage, Serge L.
, p. 8953 - 8956 (1995)
The novel deoxyribonucleoside analogues 1a,b have been synthesized in a straightforward manner from 2-deoxy-D-ribose.These modified nucleosides have also been converted to the phosphoramidite derivatives 13a,b and 14a,b for potential incorporation into ol
Synthesis of (2-deoxy-α- and -β-D-erythro-pentofuranosyl)(thymin-1-yl)alkanes and their incorporation into oligodeoxyribonucleotides. Effect of nucleobase-sugar linker flexibility on the formation of DNA-DNA and DNA-RNA hybrids
Boal, Jila H.,Wilk, Andrzej,Scremin, Carlo L.,Gray, Glenn N.,Phillips, Lawrence R.,Beaucage, Serge L.
, p. 8617 - 8626 (2007/10/03)
On the basis of modeling studies, the (2-deoxy-α- and β-D-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-D-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-0-p-toluoyl-D-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b-30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3′ → 5′)- or a (3′ → 3′)-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3′ → 3′)-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its complementary unmodified RNA sequence (ΔTm = 6°C) than for the corresponding DNA sequence (ΔTm = 10°C). This hybrid was, however, thermodynamically less stable than the duplex having unmodified α-2′-deoxythymidine similarly incorporated into 31 (ΔΔTm = 3°C).
