Oxidation of uric acid. 1. Structural revision of uric acid glycols

Poje, M.; Paulus, E. F.; Ročić, Boris

doi:10.1021/jo01289a014

Cited by 20 publications

(9 citation statements)

References 2 publications

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“…We originally proposed that the M − 10 product is a guanidinohydantoin (Gh) nucleoside that would likely be present as a mixture of two epimers (). Data presented herein is consistent with a more complex view in which Gh participates in a slow and reversible isomerization to two epimers of iminoallantoin (Ia, Scheme ) in a fashion analogous to that found in the oxidation of uric acid and other purine derivatives ( − ). The mixture of Gh + Ia is also subject to further oxidation and to base hydrolysis.…”

Section: Introductionsupporting

confidence: 88%

Characterization of Hydantoin Products from One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine in a Nucleoside Model

Luo

Muller

Rachlin

et al. 2001

Chem. Res. Toxicol.

221

322

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Use of one-electron oxidants such as Na(2)IrCl(6) to oxidize 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) residues in oligodeoxynucleotides was previously shown to lead to predominant formation of a base lesion of mass M - 10 compared to starting material [Duarte et al. (1999) Nucleic Acids Res. 27, 596-502]. To thoroughly characterize the structure of this lesion, the oxidation of the nucleoside 9-N-(2',3',5'-tri-O-acetyl-beta-D-erythro-pentanosyl)-8-oxo-7,8-dihydroguanine with one-electron oxidants at pH 2-4 was used as a model for duplex DNA oxidation of OG residues. (1)H NMR and H,H COSY NMR studies in CD(3)OD along with LC-ESI-MS/MS fragmentation analysis are consistent with the assignment of the M - 10 species as a mixture of two pH-dependent equilibrating isomers, a guanidinohydantoin (Gh) and an iminoallantoin (Ia) nucleoside, both present as mixtures of epimers at the C5 position of the hydantoin ring, i.e., four total isomers are formed. The Gh/Ia mixture is formed from hydration and decarboxylation of the initially formed intermediate 5-hydroxy-8-oxo-7,8-dihydroguanosine, a species that is also produced by four-electron oxidation (e.g., singlet oxygen) of guanosine. The product mixture can be further oxidized to a species designated Ia(ox), a hydrolytically unstable material at pH 7 that has been characterized by ESI-MS and (1)H NMR. Competition studies with 8-oxo-7,8-dihydroadenosine placed the redox potential of Gh/Ia at about 1.0 V vs NHE. These studies provide important information concerning the structures of lesions obtained when OG, a "hot spot" for oxidative damage, serves as a "hole trap" in long-range electron-transfer studies.

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Section: Introductionsupporting

confidence: 88%

Characterization of Hydantoin Products from One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine in a Nucleoside Model

Luo

Muller

Rachlin

et al. 2001

Chem. Res. Toxicol.

221

322

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“…The physical-chemical characteristics and the 1 H NMR spectrum of compound 13a are consistent with the literature data for the 1,3-dimethylgidantoin [25]. Hydantoins 13b-d are described in the literature [26][27][28] but were characterized only by the element analysis and melting points (13b -boiling point). So, we have characterized compounds 13b-d by 1 H NMR spectroscopy.…”

Section: Sep-oct 2006supporting

confidence: 82%

Synthesis of first representatives of 3,3′-bi(6,8-dialkyl-2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones)

Sigachev

Кравченко

Газиева

et al. 2006

Journal of Heterocyclic Chemistry

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The first representatives of 3,3′‐bi(2,4‐dioxa‐6,8‐diazabicyclo[3.3.0]octan‐7‐ones) have been synthesized by a reaction of glyoxal as form of 2,2′‐bi(4,5‐dihydroxy‐1,3‐dioxalane) with N,N′‐dialkylureas. Their structures have been supported by X‐ray analysis. 1,3‐Dialkylimidazolidine‐2,4‐diones (hydantoins) have been isolated as by‐products and their formation mechanism has been experimentally confirmed.

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“…5-Ethyl-5-phenylhydantoin has been synthesised with deuterium labelling at the methyl group (71a) or in the phenyl group (71b) or with a 14 C-label at the C-4 position (71c) ( Figure 13) during synthesis of the antimuscarinic drug trimebutine and its metabolites with deuterium and 14 C labels [107]. The symmetric 5,5-cyclic disubstituted spirodihydantoin has been synthesised with 13 C and 15 N labels in one half of the molecule (74a) [108] using a method by Poje et al [109] (Figure 13, Scheme 22). Reaction of 4,5,6(1H)-pyrimidinetrione 72 (79), which was converted to the sulphonyl chloride (80).…”

Section: Scheme 19mentioning

confidence: 99%

Synthesis, NMR analysis and applications of isotope-labelled hydantoins

Patching¹

2017

J Diagn Imaging Ther

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This review concerns methods of synthesis, NMR analysis and applications of isotope-labelled hydantoins. The hydantoin moiety is present in natural products and in extraterrestrial ice, indicating this to be an important compound in prebiotic chemistry. Bacterial transport proteins that scavenge hydantoins have been identified, isolated and characterised with isotope-labelling of hydantoins as an essential requirement to achieve this. These are Mhp1 from Microbacterium liquefaciens and PucI from Bacillus subtilis, transporting 5-arylsubstituted hydantoins and allantoin, respectively. The hydantoin ring is a useful centre in synthetic chemistry, especially for combinatorial chemistry, multicomponent reactions and in diversity-oriented synthesis. It is also found in pharmacologically active molecules, such as the anticonvulsant phenytoin. Hydantoins synthesised with isotope labels include hydantoin itself, allantoin, other 5-monosubstituted derivatives, phenytoin, other 5,5-disubstituted derivatives, N-substituted derivatives and other more complex molecules with multiple substituents. Analysis of isotope-containing hydantoins by NMR spectroscopy has been important for confirming purity, labelling integrity, specific activity and molecule conformation. Isotope-labelled hydantoins have been used in a range of biological, biomedical, food and environmental applications including metabolic and in vivo tissue distribution studies, biochemical analysis of transport proteins, identification and tissue distribution of drug binding sites, drug metabolism and pharmacokinetic studies and as an imaging agent.

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Oxidation of uric acid. 1. Structural revision of uric acid glycols

Cited by 20 publications

References 2 publications

Characterization of Hydantoin Products from One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine in a Nucleoside Model

Characterization of Hydantoin Products from One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine in a Nucleoside Model

Synthesis of first representatives of 3,3′-bi(6,8-dialkyl-2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones)

Synthesis, NMR analysis and applications of isotope-labelled hydantoins

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