A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides XVI)

Matsuda, Akira; Muneyama, Kei; Nishida, Takako; Sato, Tatsuo; Ueda, Tohru

doi:10.1093/nar/3.12.3349

Cited by 25 publications

(11 citation statements)

References 8 publications

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“…The ( R ) and ( S ) epimers of 8,5'-cycloadenosine, and their 2',3'-O-isopropylidene derivatives, were synthesized essentially as described by Matsuda et al [5].…”

Section: Methodsmentioning

confidence: 99%

NMR Studies on the syn‐anti Dynamic Equilibrium in Purine Nucleosides and Nucleotides

Stolarski

Dudycz

Shugar

1980

European Journal of Biochemistry

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The s.yn + anti equilibrium conformation about the glycosidic bond of purine nucleosides and 5'-nucleotides in different solvent systems has been investigated by means of 'H NMR spectroscopy. Quantitative values for the conformer populations were improved, relative to previous results, by a detailed study of, and a resultant derived correction for, the influence of the sugar exocyclic group carbons were employed to evaluate approximately the glycosidic angles x of the nucleosides in the conformations s,yn and anti. A critical examination is made of the applicability of relaxation methods, involving analysis of spin-lattice relaxation time of protons ( T I ) and the Overhauser effect, to determine the conformation of the base about the glycosidic bond; interpretations are provided for the lack of agreement between these methods and those based on chemical shifts in the present study. The foregoing results are also applied to an examination of the effect of the conformation of the base about the glycosidic bond on the enzymatic reactions catalyzed by 5'-nucleotidase and adenosine deaminase.We have previously described a procedure [l] for evaluation of the syn-anti conformer populations in nucleosides from the chemical shifts of the sugar protons, in particular of H-2'. Under conditions where there is a rapid exchange, on the N M R time-scale, between these two conformations, the observed chemical shift of H-2' is the mean of those for the fixed conformations syn and anti: dsVn and d o n t i , fiobs = Psyn d s y n + Punri d u n t i

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“…The ( R ) and ( S ) epimers of 8,5'-cycloadenosine, and their 2',3'-O-isopropylidene derivatives, were synthesized essentially as described by Matsuda et al [5].…”

Section: Methodsmentioning

confidence: 99%

NMR Studies on the syn‐anti Dynamic Equilibrium in Purine Nucleosides and Nucleotides

Stolarski

Dudycz

Shugar

1980

European Journal of Biochemistry

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“…This derivative was subsequently converted to 5Ј-phenylthio-3Ј-O-TBDMS-2Ј,5Ј-dideoxyadenosine (4) (95% yield) (36), which was submitted to photolysis at 254 nm in acetonitrile; purged with argon; and in the presence of trimethyl phosphite, irradiated by a 400-watt medium-pressure mercury lamp with a quartz filter for 30 h to afford 8,5Ј-cyclo-2Ј,5Ј-dideoxyadenosine (50% yield after chromatography). Our synthesis utilized a modification of a photochemical synthesis procedure (37), yielding (5ЈS)-8,5Ј-cycloadenosine, to prepare the cyclo-dA system.…”

Section: Synthesis Of (5јs)-85ј-cyclo-2ј-deoxyadenosine 5ј-o-phos-mentioning

confidence: 99%

The Oxidative DNA Lesion 8,5′-(S)-Cyclo-2′-deoxyadenosine Is Repaired by the Nucleotide Excision Repair Pathway and Blocks Gene Expression in Mammalian Cells

Brooks¹,

Wise²,

Berry³

et al. 2000

Journal of Biological Chemistry

289

329

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Xeroderma pigmentosum (XP) patients with inherited defects in nucleotide excision repair (NER) are unable to excise from their DNA bulky photoproducts induced by UV radiation and therefore develop accelerated actinic damage, including cancer, on sun-exposed tissue. Some XP patients also develop a characteristic neurodegeneration believed to result from their inability to repair neuronal DNA damaged by endogenous metabolites since the harmful UV radiation in sunlight does not reach neurons. Free radicals, which are abundant in neurons, induce DNA lesions that, if unrepaired, might cause the XP neurodegeneration. Searching for such a lesion, we developed a synthesis for 8,5-(S)-cyclo-2-deoxyadenosine (cyclo-dA), a free radical-induced bulky lesion, and incorporated it into DNA to test its repair in mammalian cell extracts and living cells. Using extracts of normal and mutant Chinese hamster ovary (CHO) cells to test for NER and adult rat brain extracts to test for base excision repair, we found that cyclo-dA is repaired by NER and not by base excision repair. We measured host cell reactivation, which reflects a cell's capacity for NER, by transfecting CHO and XP cells with DNA constructs containing a single cyclo-dA or a cyclobutane thymine dimer at a specific site on the transcribed strand of a luciferase reporter gene. We found that, like the cyclobutane thymine dimer, cyclo-dA is a strong block to gene expression in CHO and human cells. Cyclo-dA was repaired extremely poorly in NER-deficient CHO cells and in cells from patients in XP complementation group A with neurodegeneration. Based on these findings, we propose that cyclo-dA is a candidate for an endogenous DNA lesion that might contribute to neurodegeneration in XP.

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“…The reaction crude was lyophilized and then separated by chromatography on RP silica gel (water/acetonitrile 7:3). The following compounds were eluting in the order (yields are based on the recovered starting material): 25 [30] (R f = 0.91; 11 mg, 0.043 mmol; 5 %), 29 [31] (R f = 0.83; 31 mg; 0.12 mmol; 14 %), adenosine (R f = 0.62; 23 mg; 0.086 mmol; 10 %), 27 [32] (R f = 0.56; 6.4 mg; 0.026 mmol; 3 %), 31 [31] (R f = 0.56; 9.1 mg; 0.034 mmol; 4 %), adenine (R f = 0.47; 58 mg; 0.43 mmol; 50 %), 7 (R f = 0.34; 221 mg; 0.64 mmol; 43 % recovery).…”

mentioning

confidence: 99%

Selective Generation and Reactivity of 5′‐Adenosinyl and 2′‐Adenosinyl Radicals

Chatgilialoglu

Duca

Ferreri

et al. 2004

Chemistry A European J

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The reaction of hydrated electrons (e(-)(aq) with 8-bromoadenosine 7 has been investigated by radiolytic methods coupled with product studies. Pulse radiolysis revealed that one-electron reductive cleavage of the C-Br bond gives the C8 radical 8 followed by a fast radical translocation to the sugar moiety. The reaction is partitioned between C5' and C2' positions in a 60:40 ratio leading to 5'-adenosinyl radical 9 and 2'-adenosinyl radical 11. This radical translocation from C8 to different sites of the sugar moiety has also been addressed computationally by means of DFT B3LYP calculations. In addition, ketone 21 was prepared and photolyzed providing an independent generation of C2' radical 11. Both C5' and C2' radicals undergo unimolecular reactions. Radical 9 attacks adenine with a rate constant of 1.0 x 10(4) s(-1) and gives the aromatic aminyl radical 10, whereas C2' radical 11 liberates adenine with a rate constant of 1.1 x 10(5) s(-1).

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A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides XVI)

Cited by 25 publications

References 8 publications

NMR Studies on the syn‐anti Dynamic Equilibrium in Purine Nucleosides and Nucleotides

NMR Studies on the syn‐anti Dynamic Equilibrium in Purine Nucleosides and Nucleotides

The Oxidative DNA Lesion 8,5′-(S)-Cyclo-2′-deoxyadenosine Is Repaired by the Nucleotide Excision Repair Pathway and Blocks Gene Expression in Mammalian Cells

Selective Generation and Reactivity of 5′‐Adenosinyl and 2′‐Adenosinyl Radicals

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