Stability of N-glycosidic bond of (5'S)-8,5'-cyclo-2'-deoxyguanosine

scientific article

Stability of N-glycosidic bond of (5'S)-8,5'-cyclo-2'-deoxyguanosine is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1021/TX300302A
P932PMC publication ID3502650
P698PubMed publication ID23025578

P2093author name stringAshis K Basu
José A Gascón
Rajat S Das
Martha Morton
Milinda Samaraweera
P2860cites workDevelopment of the Colle-Salvetti correlation-energy formula into a functional of the electron densityQ21708802
Structure of (5′ S )-8,5′-Cyclo-2′-deoxyguanosine in DNAQ27675728
Structures of (5′ S )-8,5′-Cyclo-2′-deoxyguanosine Mismatched with dA or dTQ27677116
X-ray structure of a DNA decamer containing 7,8-dihydro-8-oxoguanineQ27730354
High-throughput analysis of the mutagenic and cytotoxic properties of DNA lesions by next-generation sequencingQ30503321
Removal of oxygen free-radical-induced 5',8-purine cyclodeoxynucleosides from DNA by the nucleotide excision-repair pathway in human cellsQ30856746
Identification and quantification of 8,5'-cyclo-2'-deoxy-adenosine in DNA by liquid chromatography/ mass spectrometryQ33423020
The 8,5'-cyclopurine-2'-deoxynucleosides: candidate neurodegenerative DNA lesions in xeroderma pigmentosum, and unique probes of transcription and nucleotide excision repairQ33554002
Evidence for the involvement of DNA repair enzyme NEIL1 in nucleotide excision repair of (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosinesQ33635477
(5'S)-8,5'-cyclo-2'-deoxyguanosine is a strong block to replication, a potent pol V-dependent mutagenic lesion, and is inefficiently repaired in Escherichia coliQ34974947
A mechanistic perspective on the chemistry of DNA repair glycosylasesQ35171800
The oxidatively induced DNA lesions 8,5'-cyclo-2'-deoxyadenosine and 8-hydroxy-2'-deoxyadenosine are strongly resistant to acid-induced hydrolysis of the glycosidic bondQ36724897
8,5'-Cyclopurine-2'-deoxynucleosides in DNA: mechanisms of formation, measurement, repair and biological effectsQ37207813
Accumulation of (5'S)-8,5'-cyclo-2'-deoxyadenosine in organs of Cockayne syndrome complementation group B gene knockout miceQ37219471
Purine 5',8-cyclonucleoside lesions: chemistry and biologyQ37827361
Repair efficiency of (5'S)-8,5'-cyclo-2'-deoxyguanosine and (5'S)-8,5'-cyclo-2'-deoxyadenosine depends on the complementary baseQ38320847
A single 8,5'-cyclo-2'-deoxyadenosine lesion in a TATA box prevents binding of the TATA binding protein and strongly reduces transcription in vivoQ38358615
Mechanistic studies on depurination and apurinic site chain breakage in oligodeoxyribonucleotidesQ40231852
Molecular electrostatic potential of the nucleic acidsQ40317072
Modeling the dissociative hydrolysis of the natural DNA nucleosidesQ43205727
Theoretical study on the stability of N-glycosyl bonds: why does N7-platination not promote depurination?Q43963959
First principles calculations of the tautomers and pK(a) values of 8-oxoguanine: implications for mutagenicity and repairQ44107144
8-Methylguanosine: a powerful Z-DNA stabilizerQ44635071
Formation of cyclonucleotides during irradiation of aqueous solutions of purine nucleotidesQ44981737
Oxygen free radical damage to DNA. Translesion synthesis by human DNA polymerase eta and resistance to exonuclease action at cyclopurine deoxynucleoside residues.Q53990151
Synthesis, miscoding specificity, and thermodynamic stability of oligodeoxynucleotide containing 8-methyl-2'-deoxyguanosine.Q54576353
Contribution to the mechanism of the acid-catalyzed hydrolysis of purine nucleosidesQ70399207
Enzyme-bound conformations of nucleotide substrates. X-ray structure and absolute configuration of 8,5'-cycloadenosine monohydrateQ71206613
Kinetics and mechanism of the acid-catalyzed hydrolysis of some purine nucleosidesQ71431754
The oxidative DNA lesion 8,5'-(S)-cyclo-2'-deoxyadenosine is repaired by the nucleotide excision repair pathway and blocks gene expression in mammalian cellsQ73763148
Synthesis and characterization of oligonucleotides containing 5',8-cyclopurine 2'-deoxyribonucleosides: (5'R)-5',8-cyclo-2'-deoxyadenosine, (5'S)-5',8-cyclo-2'-deoxyguanosine, and (5'R)-5',8-cyclo-2'-deoxyguanosineQ77752837
Influence of N7 protonation on the mechanism of the N-glycosidic bond hydrolysis in 2'-deoxyguanosine. A theoretical studyQ80261505
Measurement of (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines in DNA in vivo by liquid chromatography/isotope-dilution tandem mass spectrometryQ84134619
P433issue11
P304page(s)2451-2461
P577publication date2012-10-15
P1433published inChemical Research in ToxicologyQ473530
P1476titleStability of N-glycosidic bond of (5'S)-8,5'-cyclo-2'-deoxyguanosine
P478volume25

Reverse relations

cites work (P2860)
Q923763745',8-Cyclopurine Lesions in DNA Damage: Chemical, Analytical, Biological, and Diagnostic Significance
Q390375338-Oxo-7,8-dihydroadenine and 8-Oxo-7,8-dihydroadenosine-Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives.
Q34712058A 5', 8-cyclo-2'-deoxypurine lesion induces trinucleotide repeat deletion via a unique lesion bypass by DNA polymerase β
Q35895192An ameliorative protocol for the quantification of purine 5',8-cyclo-2'-deoxynucleosides in oxidized DNA.
Q35977207Bypass of a 5',8-cyclopurine-2'-deoxynucleoside by DNA polymerase β during DNA replication and base excision repair leads to nucleotide misinsertions and DNA strand breaks
Q37727678Epimeric 2-deoxyribose lesions: Products from the improper chemical repair of 2-deoxyribose radicals
Q46317006IRMPD Action Spectroscopy, ER-CID Experiments, and Theoretical Studies of Sodium Cationized Thymidine and 5-Methyluridine: Kinetic Trapping During the ESI Desolvation Process Preserves the Solution Structure of [Thd+Na].
Q37292625Induction of 8,5'-cyclo-2'-deoxyadenosine and 8,5'-cyclo-2'-deoxyguanosine in isolated DNA by Fenton-type reagents
Q53766705Radical-induced purine lesion formation is dependent on DNA helical topology.
Q39000410Removal of oxidatively generated DNA damage by overlapping repair pathways