95041-49-9Relevant academic research and scientific papers
DNA damage and interstrand cross-link formation upon irradiation of aryl iodide C-nucleotide analogues
Ding, Hui,Greenberg, Marc M.
experimental part, p. 535 - 544 (2010/04/26)
(Chemical Equation Presented) The 5-halopyrimidine nucleotides damageDNAupon UV-irradiation or exposure to γ-radiolysis via the formation of the 2′-deoxyuridin-5-yl σ-radical. The bromo and iodo derivatives of these molecules are useful tools for probing DNA structure and as therapeutically useful radiosensitizing agents. A series of aryl iodide C-nucleotides were incorporated into synthetic oligonucleotides and exposed to UV-irradiation and γ-radiolysis. The strand damage produced upon irradiation of DNA containing these molecules is consistent with the generation of highly reactive σ-radicals. Direct stand breaks and alkali-labile lesions are formed at the nucleotide analogue and flanking nucleotides. The distribution of lesion type and location varies depending upon the position of the aryl ring that is iodinated. Unlike 5-halopyrimidine nucleotides, the aryl iodides produce interstrand cross-links in duplex regions of DNA when exposed to γ-radiolysis or UV-irradiation. Quenching studies suggest that cross-links are produced by γ-radiolysis via capture of a solvated electron, and subsequent fragmentation to the σ-radical. These observations suggest that aryl iodide C-nucleotide analogues may be useful as probes for excess electron transfer and radiosensitizing agents.
Modular Synthesis of 4-aryl- and 4-amino-substituted benzene C-2′-Deoxyribonucleosides
Joubert, Nicolas,Urban, Milan,Pohl, Radek,Hocek, Michal
experimental part, p. 1918 - 1932 (2009/04/04)
A modular methodology for the syntheses of various 4-substituted-phenyl C-2′-deoxyribonucleosides has been developed. Coupling of toluoylated halogenose 1 with 4-bromophenylmagnesium bromide afforded the desired bis(toluoyl)-protected 1β-(4-bromophenyl)-1
Disiloxane-protected 2-deoxyribonolactone as an efficient precursor to 1,2-dideoxy-1-β-aryl-D-ribofuranoses
Wichai, Uthai,Woski, Stephen A.
, p. 1173 - 1175 (2008/02/09)
(matric presented) Aryl C-nucleosides are analogues of natural nucleosides where the bases have been replaced with aromatic moieties. Work herein describes the highly stereoselective syntheses of non-hydrogen-bonding carbocyclic derivatives using a disiloxane-protected 2-deoxy-D-ribono-1,4-lactone as a stable and readily accessible starting material. Unlike the bis(TBDMS)-protected congener, this compound enables the use of sterically congested ortho-substituted aryllithium reagents in the initial addition reaction.
An improved route to 1,2-dideoxy-β-1-phenyl-D-ribofuranose
Wichai, Uthai,Woski, Stephen A.
, p. 3465 - 3468 (2007/10/03)
An efficient synthesis of the aryl nucleoside analogue 1,2-dideoxy-β- 1-phenyl-D-ribofuranose (1) is described. This route utilizes the addition of phenyllithium to a protected 2-deoxyribonolactone followed by reduction with triethylsilane/boron trifluoride etherate to selectively produce the β- anomer. Deprotection yields the desired aryl C-nucleoside in 27% overall yield from 2-deoxy-D-ribose.
An efficient method for the synthesis of aromatic C-nucleosides
Chaudhuri, Narayan C.,Kool, Eric T.
, p. 1795 - 1798 (2007/10/02)
Reaction of diarylcadmium or diarylzinc reagents with 1,2-dideoxy-3,5-di-O-p-toluoyl-1-chloro-α-D-ribofuranose affords 3,5-di-O-protected aromatic C-nucleosides in good yields.
ERYTHROSE SESQUI-ACETALS AS ELECTROPHILES. 2-DEOXY-C-NUCLEOSIDES FROM D-GLUCOSE.
Polt, Robin,Wijayaratne, Thusitha
, p. 4831 - 4834 (2007/10/02)
Cleavage of glucosides with NaIO4 in MeOH furnishes sesqui-acetals (protected dialdehydes).Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses).Pro
