50908-40-2Relevant academic research and scientific papers
A short and efficient synthesis of 2′-deoxybenzo- and pyridoimidazole C-nucleosides
Jazouli, Mohamed,Guianvarc'h, Dominique,Soufiaoui, Mohamed,Bougrin, Khalid,Vierling, Pierre,Benhida, Rachid
, p. 5807 - 5810 (2007/10/03)
A short route to a series of 2′-deoxy-C-nucleosides featuring substituted nucleobases has been developed. The key step is the formation of the cyclized products following Mukaiyama's type amide coupling and a simple dehydration, starting from readily accessible synthons. The epimerization of the C1′-stereogenic center was avoided under mild and controlled conditions.
[(2-deoxy-α- and β-D-erythro-pentofuranosyl)thymin-1-yl] methane derivatives as potential conformational probes for altDNA oligonucleotides
Scremin,Boal,Wilk,Phillips,Beaucage
, p. 207 - 212 (2007/10/03)
The previously unknown deoxyribonucleoside analogues 2a,b have been efficiently synthesized from commercial 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose. The conversion of these nucleosides to the phosphoramidite derivatives 13a,b and 14a,b for subsequent incorporation into oligodeoxyribonucleotide analogues is also described.
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).
Preparation of Modified Nucleosides from Glucosamine: Rapid and Efficient Formal Total Synthesis of Several 2'-Deoxy C-Nucleosides
Jung, Michael E.,Trifunovich, Ivan D.,Gardiner, John M.,Clevenger, Gary L.
, p. 84 - 85 (2007/10/02)
Formal total syntheses of several 2'-deoxy C-nucleosides have been accomplished in a short and efficient process using D-glucosamine as the starting material.
