193905-26-9Relevant academic research and scientific papers
98. Studies on the Base-Pairing Properties of N7-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine (N7Gd)
Seela, Frank,Leonard, Peter
, p. 1301 - 1318 (2007/10/03)
The base-pairing properties of N7-(2-deoxy-β-D-erythro-pentofuranosyl)guanine (N7Gd; 1) are investigated. The nucleoside 1 was obtained by nucleobase-anion glycosylation. The glycosylation reaction of various 6-alkoxypurin-2-amines 3a-i with 2-deoxy-3,5-di-O-(4-toluoyl)-α-D-erythro-pentofuranosyl chloride (8) was studied. The N9/N7-glycosylation ratio was found to be 1:1 when 6-isopropoxypurin-2-amine (3d) was used, whereas 6-(2-melhoxyethoxy)purin-2-amine (3i) gave mainly the N9-nucleoside (2:1). Oligonucleotides containing compound 1 were prepared by solid-phase synthesis and hybridized with complementary strands having the four conventional nucleosides located opposite to N7Gd. According to Tm values and enthalpy data of duplex formation, a base pair between N7Gd and dG is suggested. From the possible N7Gd · dG base pair motives, Hoogsteen pairing can be excluded as 7-deaza-2′-deoxyguanosine forms the same stable base pair with N7Gd as dG.
