5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination.

5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Research Abstract Details 

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5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Abstract Text:

Ming Qian,Rainer Glaser,

5-Cyanoamino-4-imidazolecarboxamide 4a (R = CH2-O-CH2-CH2-OH) has been synthesized, purified, and fully characterized by MS, MS/MS, HRMS, IR spectroscopy, and by 1H and 13C NMR spectroscopy. It is shown that cyclization of 4a yields the guanine 6a and the isoguanine 12a. Our findings provide experimental evidence in support of our hypothesis that the formation of oxanine and xanthine in nitrosative guanine deamination may proceed via pyrimidine ring-opened intermediates. The observed formation of 6a from the amide 4a (XH2 = NH2) shows that, in analogy, oxanine can be formed from 3 (XH = OH). The formation of 12a from 4a reveals for the first time the possibility that oxanine might be formed by a second pathway that involves electrocyclic reaction of 3. Finally, the new chemistry suggests the possibility for a new dG-to-dG cross-link.

5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Publishing Authors By Initials

M Qian,R Glaser,

For similar organic chemicals: nitriles research abstracts see: organic chemicals: nitriles research

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5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 2274-5

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 3

MONTH: Mar

YEAR: 2004

5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Keywords Mesh Terms:

KEYWORDS: Nitriles

MESH TERMS: chemistry

Chemical & Substance for Abstract: 5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Information

Substance Name: Guanine

Registry Number: 73-40-5

Grant and Affiliation Information for 5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination.

AFFILIATION: University of Missouri-Columbia, Department of Chemistry, 605 South College Avenue, Columbia, Missouri 65211, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM61027

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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