Oligonucleotides Containing Disaccharide Nucleosides

Abstract

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 DT m of 0.5 to À 1.48 for DNA/RNA and a DT m of À 0.8 to À 4.78 for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH 2 ÀC(5'') group has a beneficial effect on duplex stability.

Effective Anomerisation of 2′‐Deoxyadenosine Derivatives During Disaccharide Nucleoside Synthesis

“…Several other fully acylated monosaccharide derivatives of D-and L-arabinofuranoses, D-erythrofuranose and D-ribopyranose have been successfully used in the same reaction. [9] This general methodology has additionally been extended to the synthesis of pyrimidine 3'-O-(b-D-ribofuranosyl)-2'-deoxynucleosides. [10] The coupling of 5'-O-(tert-butyldiphenylsilyl)thymidine (1a) with fully acylated sugar (2) in the presence of tin tetrachloride under standard conditions (1,2-dichloroethane, 0°C, under nitrogen) gave the desired product (3) in 79% yield [10] (Scheme 1).…”

Novel group of tyrosyl-DNA-phosphodiesterase 1 inhibitors based on disaccharide nucleosides as drug prototypes for anti-cancer therapy

“…Compounds 1–49 ( Table 1 ) were prepared according to the literature procedures: 1, 3–4 32–37 , 2 38 , 5–11 32 , 12 – 21 39 , 22–23 , 34 40 , 24–27 41 , 42 , 32–33 41–44 , 35–37 41 , 42 , 28–29, 38–42 28–29 , 30–31 40 , 43–49 43 , 44 . The presence of fluorine atoms in position 5 of pyrimidine residue in compounds 19 , 20 , 49 is confirmed by spin-spin coupling constants between 19 F and 1 H in 1 H-NMR spectra ( J H-F ) and between 19 F and 13 C in 13 C-NMR spectra ( J C-F ).…”

Poly(ADP-Ribose)—A Unique Natural Polymer Structural Features, Biological Role and Approaches to the Chemical Synthesis

“…[3,[50][51][52][53] Introduction of labile pyrophosphate bond requires more mild conditions. Formation of pyrophosphate linkages by various chemical methods is widely-known and well-described in the literature.…”