85754-75-2Relevant academic research and scientific papers
Modified Nucleotides for Discrimination between Cytosine and the Epigenetic Marker 5-Methylcytosine
Von Watzdorf, Janina,Leitner, Kim,Marx, Andreas
supporting information, p. 3229 - 3232 (2016/03/12)
5-Methyl-2′-deoxycytosine, the most common epigenetic marker of DNA in eukaryotic cells, plays a key role in gene regulation and affects various cellular processes such as development and carcinogenesis. Therefore, the detection of 5mC can serve as an important biomarker for diagnostics. Here we describe that modified dGTP analogues as well as modified primers are able to sense the presence or absence of a single methylation of C, even though this modification does not interfere directly with Watson-Crick nucleobase pairing. By screening several modified nucleotide scaffolds, O6-modified 2′-deoxyguanosine analogues were identified as discriminating between C and 5mC. These modified nucleotides might find application in site-specific 5mC detection, for example, through real-time PCR approaches.
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.
