The mechanism for the conversion of uric acid into allantoin and dehydro-allantoin

Poje, M.; Sokolić-Maravić, Lea

doi:10.1016/s0040-4020(01)87480-9

Cited by 39 publications

(27 citation statements)

References 33 publications

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“…On the other hand, the lack of observation of two diastereosmers in the case of ROP-1 is a mystery that still awaits resolution. Finally, the current work strongly supports the postulated spironature of the alkali labile intermediate [8] observed in the oxidation of uric acid under alkaline conditions (12,13).…”

supporting

confidence: 84%

“…In assigning these structures we noted that there was a parallel with the case of uric acid whose oxidation in alkali had been studied most recently by Poje and Sokolic-Maravic (12,13). The authors concluded through an indirect proof that one of the degradation products was 8, but they noted that it underwent further rapid degradation in the alkaline medium to give noncyclic products.…”

Section: Introductionmentioning

confidence: 88%

See 1 more Smart Citation

Synthetic and oxidative studies on 8-(arylamino)-2'-deoxyguanosine and -guanosine derivatives.

Johnson

Huang²,

Yu³

1994

Environ Health Perspect

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Facile aerial oxidation is a general feature of guanine ribo-and 2'-deoxyribonucleosides that are substituted at the 8-position by an aminoaryl group. In previous work, it had been suggested that two of the major oxidation products are a pair of diastereomers having a spiro structure. These were presumed to be related by a chiral difference at the spiro carbon atom. The pattern of the oxidative process involves a contraction of the pyrimidine ring. It was thought to be analogous to that suggested by other investigators for the oxidation of uric acid, but for which no really definitive evidence had been presented. We have been able now to isolate in a crystalline state one of the diastereomers produced by the aerial oxidation of 8-phenylaminoguanosine under alkaline conditions. Analysis by X-ray diffraction has now confirmed the type of spiro structure promulgated previously. These findings also imply that spiro compounds are likely to be produced during the aerial oxidation of any 8-arylaminoguanine nucleoside or 2'-deoxynucleoside. In addition, this work adds considerable weight to the results of Poje and Sokolic-Maravic who proposed that a spiro intermediate is produced during the aerial oxidation of uric acid (12,13). However, they found this compound to be unstable to base, in contrast to the arylaminoguanine oxidation products. In the course of the above work we showed that the 8-arylamino derivatives of guanosine can be converted by the Barton deoxygenation method to the corresponding 2'-deoxyribonucleosides. This makes available a number of the latter compounds, which are not easily prepared by other methods.

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supporting

confidence: 84%

Section: Introductionmentioning

confidence: 88%

Synthetic and oxidative studies on 8-(arylamino)-2'-deoxyguanosine and -guanosine derivatives.

Johnson

Huang²,

Yu³

1994

Environ Health Perspect

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“…Therefore, IIb is identified as 3-(3,5-di-O-Ac-2-deoxy-␤-D-erythro-pentofuranosyl)-5-iminoimidazolidine-2,4-dione. Further, as has been reported previously for substituted 5-iminoimidazolidine-2,4-dione compounds, strong acid or base treatment will cause ring expansion to yield s-triazine structures, including oxonic acid and 5-azauracil, by mechanisms that are not clearly understood (28). Indeed, acid hydrolysis of IIb led to release of an aglycon that was identified as 5-azauracil based on an identical GC/MS retention time and fragmentation pattern as authentic 5-azauracil (Table 1), thus further indirectly supporting the proposed structure for IIb.…”

Section: Characterization Of IImentioning

confidence: 89%

“…There are several important models for the oxidation of 8-oxodGuo: (i) the alkaline potassium permanganate or iodine-mediated oxidation of uric acid; (ii) the electrochemical oxidation of 8-oxoGua; and (iii) the photooxidation of 8-oxodGuo. Alkaline oxidation of uric acid leads to the formation of allantoin and dehydroallantoin as major products (28). Electrochemical oxidation of 8-oxoGua results in formation of 2,5-diaminoimidazol-4-one (IIa) and 5-guanidinohydantoin (29).…”

mentioning

confidence: 99%

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

Niles

Burney

Singh

et al. 1999

Proc. Natl. Acad. Sci. U.S.A.

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Of the DNA bases, peroxynitrite (ONOO ؊ ) is most reactive toward 2-deoxyguanosine (dGuo), but even more reactive with 8-oxo-7,8-dihydro-2-deoxyguanosine (8-oxodGuo), requiring a 1,000-fold excess of dGuo to provide 50% protection against the reaction with 8-oxodGuo. Therefore, it seems reasonable that 8-oxodGuo is a potentially important target in DNA and that the structures of the reaction products with ONOO ؊ should be characterized.

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“…Different binding motifs in guanidinium urate and 8-azaxanthinate [2], which presumably reflect the location of negative charge [3], are related by 180° rotation about the N1-C4 axis; the conformational flexibility of Argl76, Gln228, and Phel59 residues in the active cleft allows an induced fit for binding. It is now clear how the stereospecificity of uricase reaction may arise [4][5][6][7][8]. Urate fits snugly into the active pocket, exposing the si-si face with effectively desolvated imidazolone subnucleus to the oxidative attack.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of guanidinium urate monohydrate, C5H3N4O3(CH6N3) · H2O

Poje

Vicković

2000

Zeitschrift Für Kristallographie - New Crystal Structures

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The mechanism for the conversion of uric acid into allantoin and dehydro-allantoin

Cited by 39 publications

References 33 publications

Synthetic and oxidative studies on 8-(arylamino)-2'-deoxyguanosine and -guanosine derivatives.

Synthetic and oxidative studies on 8-(arylamino)-2'-deoxyguanosine and -guanosine derivatives.

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

Crystal structure of guanidinium urate monohydrate, C5H3N4O3(CH6N3) · H2O

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