15717-45-0Relevant articles and documents
A novel nitration product formed during the reaction of peroxynitrite with 2',3',5'-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-nitro-N'-[1-(2,3,5- tri-O-acetyl-β-D-erythro-pentofuranosyl)-2,4-dioxoimidazolidin-5- ylidene]guanidine
Niles, Jacquin C.,Wishnok, John S.,Tannenbaum, Steven R.
, p. 390 - 396 (2000)
A novel nitration product, formed during the reaction of peroxynitrite with 2',3',5'-tri-O-acetyl-7,8-dihydro-8-oxoguanosine, has been characterized using a combination of UV/vis, CD, and NMR spectroscopy and mass spectrometry. This compound has been identified as N-nitro-N'-[1-(2,3,5-tri- P-O-acetyl-β-D-erythro-pentofuranosyl)-2,4-dioxoimidazolin-5- ylidene]guanidine (IV). Upon base hydrolysis, IV releases nitroguanidine (IVa) and an intermediate, 1-(2,3,5-tri-O-acetyl-β-D-erythro- pentofuranosyl)-5-iminoimidazolidine-2,4-dione (IVb). This intermediate is ultimately hydrolyzed to the stable 3-(2,3,5-tri-O-acetyl-β-D-erythro- pentofuranosyl)oxaluric acid (IVc). IV can be reduced by sodium borohydride to a pair of stable diastereomers (IV(red)). The formation of this product is rationalized in terms of initial oxidation of 2',3',5'-tri-O-acetyl-7,8- dihydro-8-oxoguanosine to a quinonoid diimine intermediate, 3. Nucleophilic attack at C5 of 3 by peroxynitrite leads to formation of a C5-oxyl radical species, 5, which then undergoes a series of rearrangements to yield an ylidene radical, 7. Combination of this radical species with nitrogen dioxide results in the formation of product IV.
Pyridine-free and solvent-free acetylation of nucleosides promoted by molecular sieves
Sá, Marcus Mandolesi,Meier, Lidiane
, p. 3474 - 3478 (2006)
A practical method for the acetylation of purine and pyrimidine nucleosides employing a combination of acetic anhydride and potassium-exchanged molecular sieves is described. Besides the high yields obtained for the acylated nucleosides, the procedure is simple, inexpensive and environmentally benign, avoiding the use of pyridine or co-solvents as additives. Georg Thieme Verlag Stuttgart.
Tautomerism in 8-Nitroguanosine Studied by NMR and Theoretical Calculations
Barbosa, Thaís M.,Rittner, Roberto,Alexander, Katie,Cosstick, Richard,Abraham, Raymond J.
, p. 53 - 63 (2016/03/01)
The guanine base in DNA, due to its low oxidation potential, is particularly sensitive to chemical modifications. A large number of guanine lesions have been characterized and studied in some detail due to their relationship with tissue inflammations. Nevertheless, one example of these lesions is the formation of 8-nitro-guanosine, but the NMR data of this compound was only partially interpreted. A comprehensive study of the two possible tautomeric forms, through a detailed characterization of this compound, has implications for its base pairing properties. The target compound was obtained through a synthetic sequence of five steps, where all intermediates were fully characterized using spectral data. The analysis of the two tautomers was then evaluated through NMR spectroscopy and theoretical calculations of the chemical shifts and NH coupling constants, which were also compared with the data from guanosine.
RNA INCLUDING NUCLEOSIDE COMPOUND, METHOD FOR REGULATING AMOUNT OF PROTEIN PRODUCED FROM THE RNA, AND NUCLEOSIDE COMPOUND
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Page/Page column, (2013/03/26)
An RNA of the present invention is an RNA containing a 5′ cap structure and a coding region having a 5′ initiation codon and a 3′ stop codon on both ends of the coding region, the RNA having a nucleoside compound introduced at a site selected from among the 5′ cap structure and 10 bases from a 5′ end of the RNA, wherein the nucleoside compound is such that a group is attached to (i) a carbon atom at position 8 of a purine nucleus or (ii) a carbon atom at position 5 or 6 of a pyrimidine nucleus, the group being represented by formula (I): [in-line-formulae]A-X═X-#??(I)[/in-line-formulae] where A represents an aryl group or a heteroaryl group, # represents a site where the group represented by the formula (I) is attached to the carbon atom at the position 8 of the purine nucleus or the carbon atom at the position 5 or 6 of the pyrimidine nucleus, and two Xs, which are identical to or different from each other, each represents a nitrogen atom or CH whose H may be substituted by alkyl.
