127553-36-0Relevant academic research and scientific papers
Synthesis of 4-substituted 1H-benzimidazole 2'-deoxyribonucleosides and utility of the 4-nitro compound as universal base
Seela,Bourgeois,Rosemeyer,Wenzel
, p. 488 - 498 (1996)
The stereoselective synthesis of 4-substituted 1H-benzimidazole 2'-deoxyribonucleosides is described. Regioisomeric (N1 and N3) β-D-deoxyribonucleosides 2a-c and 3a-c were formed. 13C-NMR Chemical shifts of the 1H-benzimid
Glycosylation reactions of 6-nitro-1,3-dideazapurine and 6-nitro-1-deazapurine
Devlin,Lacrosaz-Rouanet,Vo,Jebaratnam
, p. 1601 - 1604 (1995)
In glycosylations utilizing SnCl4 activation or S(N)2 displacement of the α-chlorosugar, two closely related purines, namely 6-nitro-1,3-dideazapurine 1 and 6-nitro-1-deazapurine 2, give different distributions of isomeric products.
Silver(I)-mediated cytosine self-pairing is preferred over hoogsteen-type base pairs with the artificial nucleobase 1,3-dideaza-6-nitropurine
Megger, Dominik A.,Mueller, Jens
experimental part, p. 27 - 38 (2010/07/06)
A 2′-deoxyribonucleoside containing 1,3-dideaza-6-nitropurine was synthesized and incorporated into oligonucleotides. The acid-base properties of this nucleoside and the corresponding N9-methylated derivative were investigated by pD-dependent 1H NMR spectroscopy. A possible formation of Hoogsteen-type base pairs with cytosine was studied by ultraviolet (UV) and circular dichroism (CD) spectroscopy in the presence and absence of Ag(I) and under neutral and acidic conditions, respectively. In each case, no indication for the formation of Hoogsteen-type base pairs was obtained, which is attributed to the higher affinity of cytosine to form self-complementary hemi-protonated base pairs under acidic conditions and metal-mediated homo base pairs in presence of Ag(I), respectively.
