Computational studies of electronic circular dichroism spectra predict absolute configuration assignments for the guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin

scientific article published on June 2015

Computational studies of electronic circular dichroism spectra predict absolute configuration assignments for the guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1016/J.TETLET.2014.12.052
P932PMC publication ID4472374
P698PubMed publication ID26097262
P5875ResearchGate publication ID277882201

P50authorCynthia J. BurrowsQ28823528
P2093author name stringAaron M Fleming
Anita M Orendt
Omar Alshykhly
P2860cites workDevelopment of the Colle-Salvetti correlation-energy formula into a functional of the electron densityQ21708802
One-electron oxidation reactions of purine and pyrimidine bases in cellular DNAQ27004254
Crystal Structure of DNA Polymerase β with DNA Containing the Base Lesion Spiroiminodihydantoin in a Templating PositionQ27682343
Thermodynamic profiles and nuclear magnetic resonance studies of oligonucleotide duplexes containing single diastereomeric spiroiminodihydantoin lesionsQ30586686
Reconciliation of chemical, enzymatic, spectroscopic and computational data to assign the absolute configuration of the DNA base lesion spiroiminodihydantoinQ30692305
Formation of 13C-, 15N-, and 18O-Labeled Guanidinohydantoin from Guanosine Oxidation with Singlet Oxygen. Implications for Structure and MechanismQ30883974
Characterization of 2'-deoxyguanosine oxidation products observed in the Fenton-like system Cu(II)/H2O2/reductant in nucleoside and oligodeoxynucleotide contextsQ33561899
Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectraQ33648857
Direct oxidation of guanine and 7,8-dihydro-8-oxoguanine in DNA by a high-valent chromium complex: a possible mechanism for chromate genotoxicityQ34517738
Comparison of Transition Metal-Mediated Oxidation Reactions of Guanine in Nucleoside and Single-Stranded Oligodeoxynucleotide ContextsQ34812595
Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions.Q35830861
Iminohydantoin lesion induced in DNA by peracids and other epoxidizing oxidants.Q37211491
Chemical and biological consequences of oxidatively damaged guanine in DNA.Q37975286
Oxidation of guanine and 8-oxo-7,8-dihydroguanine by carbonate radical anions: insight from oxygen-18 labeling experimentsQ46597387
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Quantum mechanical continuum solvation models.Q55041134
Solvent Effect on Optical Rotation: A Case Study of Methyloxirane in WaterQ59706628
Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-Oxo-7,8-dihydroguanosineQ73799886
Oxidative Nucleobase Modifications Leading to Strand ScissionQ77646680
Nuclear magnetic resonance studies of the 4R and 4S diastereomers of spiroiminodihydantoin 2'-deoxyribonucleosides: absolute configuration and conformational featuresQ79238080
Guanine oxidation: one- and two-electron reactionsQ79769529
Assignment of absolute configurations of the enantiomeric spiroiminodihydantoin nucleobases by experimental and computational optical rotatory dispersion methodsQ79909134
Targeted guanine oxidation by a dinuclear copper(II) complex at single stranded/double stranded DNA junctionsQ80170323
Absolute stereochemistry and preferred conformations of urate degradation intermediates from computed and experimental circular dichroism spectraQ84290090
A single nuclease-resistant linkage in DNA as a versatile tool for the characterization of DNA lesions: application to the guanine oxidative lesion "G+34" generated by metalloporphyrin/KHSO(5) reagentQ95422757
P433issue23
P304page(s)3191-3196
P577publication date2015-06-01
P1433published inTetrahedron LettersQ903432
P1476titleComputational studies of electronic circular dichroism spectra predict absolute configuration assignments for the guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin
P478volume56

Reverse relations

cites work (P2860)
Q358714535-Carboxamido-5-formamido-2-iminohydantoin, in Addition to 8-oxo-7,8-Dihydroguanine, Is the Major Product of the Iron-Fenton or X-ray Radiation-Induced Oxidation of Guanine under Aerobic Reducing Conditions in Nucleoside and DNA Contexts
Q39018239Formation and processing of DNA damage substrates for the hNEIL enzymes
Q36728705Guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin induces mutations when bypassed by DNA polymerases and is a substrate for base excision repair
Q46413562Interrogation of Base Pairing of the Spiroiminodihydantoin Diastereomers Using the α-Hemolysin Latch
Q39020441Rates of chemical cleavage of DNA and RNA oligomers containing guanine oxidation products

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