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Namehelp_outline
an N1-methyl-2ʼ-deoxyadenosine in double-stranded DNA
Identifier
RHEA-COMP:14236
Reactive part
help_outline
- Name help_outline N1-methyl-dAMP residue Identifier CHEBI:139096 Charge 0 Formula C11H14N5O5P SMILEShelp_outline [N+]=1(C=NC2=C(N=CN2[C@@H]3O[C@H](COP(*)(=O)[O-])[C@H](C3)O*)C1N)C 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-methyladenine Identifier CHEBI:18083 (CAS: 5142-22-3) help_outline Charge 0 Formula C6H7N5 InChIKeyhelp_outline HPZMWTNATZPBIH-UHFFFAOYSA-N SMILEShelp_outline Cn1cnc2ncnc2c1N 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
a 2ʼ-deoxyribose 5ʼ-monophosphate in double-stranded DNA
Identifier
RHEA-COMP:14231
Reactive part
help_outline
- Name help_outline a 2ʼ-deoxyribose 5ʼ-monophosphate residue Identifier CHEBI:139095 Charge -1 Formula C5H8O6P SMILEShelp_outline OC1O[C@H](COP(*)(=O)[O-])[C@H](C1)O* 2D coordinates Mol file for the small molecule Search links Involved in 8 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:55612 | RHEA:55613 | RHEA:55614 | RHEA:55615 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Structural basis for enzymatic excision of N1-methyladenine and N3-methylcytosine from DNA.
Leiros I., Nabong M.P., Grosvik K., Ringvoll J., Haugland G.T., Uldal L., Reite K., Olsbu I.K., Knaevelsrud I., Moe E., Andersen O.A., Birkeland N.K., Ruoff P., Klungland A., Bjelland S.
N(1)-methyladenine (m(1)A) and N(3)-methylcytosine (m(3)C) are major toxic and mutagenic lesions induced by alkylation in single-stranded DNA. In bacteria and mammals, m(1)A and m(3)C were recently shown to be repaired by AlkB-mediated oxidative demethylation, a direct DNA damage reversal mechanis ... >> More
N(1)-methyladenine (m(1)A) and N(3)-methylcytosine (m(3)C) are major toxic and mutagenic lesions induced by alkylation in single-stranded DNA. In bacteria and mammals, m(1)A and m(3)C were recently shown to be repaired by AlkB-mediated oxidative demethylation, a direct DNA damage reversal mechanism. No AlkB gene homologues have been identified in Archaea. We report that m(1)A and m(3)C are repaired by the AfAlkA base excision repair glycosylase of Archaeoglobus fulgidus, suggesting a different repair mechanism for these lesions in the third domain of life. In addition, AfAlkA was found to effect a robust excision of 1,N(6)-ethenoadenine. We present a high-resolution crystal structure of AfAlkA, which, together with the characterization of several site-directed mutants, forms a molecular rationalization for the newly discovered base excision activity. << Less
EMBO J 26:2206-2217(2007) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.