Reaction participants Show >> << Hide
-
Namehelp_outline
a N2,3-etheno-2ʼ-deoxyguanosine in double-stranded DNA
Identifier
RHEA-COMP:20175
Reactive part
help_outline
- Name help_outline N2,3-etheno-dGMP residue Identifier CHEBI:233192 Charge -1 Formula C12H11N5O6P SMILEShelp_outline C1(=O)NC=2N(C3=C1N=CN3[C@@H]4O[C@H](COP(=O)(*)[O-])[C@@H](O*)C4)C=CN2 2D coordinates Mol file for the small molecule Search links Involved in 1 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 N2,3-ethenoguanine Identifier CHEBI:134095 (CAS: 62962-42-9) help_outline Charge 0 Formula C7H5N5O InChIKeyhelp_outline OSXKHFTZRHDUJN-UHFFFAOYSA-N SMILEShelp_outline O=C1NC=2N(C=3NC=NC31)C=CN2 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
-
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
Cross-references
| RHEA:83623 | RHEA:83624 | RHEA:83625 | RHEA:83626 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
Publications
-
All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase.
Dosanjh M.K., Chenna A., Kim E., Fraenkel-Conrat H., Samson L., Singer B.
We have previously reported that human cells and tissues contain a 1,N6-ethenoadenine (epsilon A) binding protein, which, through glycosylase activity, releases both 3-methyladenine (m3A) and epsilon A from DNA treated with methylating agents or the vinyl chloride metabolite chloroacetaldehyde, re ... >> More
We have previously reported that human cells and tissues contain a 1,N6-ethenoadenine (epsilon A) binding protein, which, through glycosylase activity, releases both 3-methyladenine (m3A) and epsilon A from DNA treated with methylating agents or the vinyl chloride metabolite chloroacetaldehyde, respectively. We now find that both the partially purified human epsilon A-binding protein and cell-free extracts containing the cloned human m3A-DNA glycosylase release all four cyclic etheno adducts--namely epsilon A, 3,N4-ethenocytosine (epsilon C), N2,3-ethenoguanine (N2,3-epsilon G), and 1,N2-ethenoguanine (1,N2-epsilon G). Base release was both time and protein concentration dependent. Both epsilon A and epsilon C were excised at similar rates, while 1,N2-epsilon G and N2,3-epsilon G were released much more slowly under identical conditions. The cleavage of glycosyl bonds of several heterocyclic adducts as well as those of simple methylated adducts by the same human glycosylase appears unusual in enzymology. This raises the question of how such a multiple, divergent activity evolved in humans and what may be its primary substrate. << Less
Proc Natl Acad Sci U S A 91:1024-1028(1994) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
-
Release of N2,3-ethenoguanine from chloroacetaldehyde-treated DNA by Escherichia coli 3-methyladenine DNA glycosylase II.
Matijasevic Z., Sekiguchi M., Ludlum D.B.
The human carcinogen vinyl chloride is metabolized in the liver to reactive intermediates which form N2,3-ethenoguanine in DNA. N2,3-Ethenoguanine is known to cause G----A transitions during DNA replication in Escherichia coli, and its formation may be a carcinogenic event in higher organisms. To ... >> More
The human carcinogen vinyl chloride is metabolized in the liver to reactive intermediates which form N2,3-ethenoguanine in DNA. N2,3-Ethenoguanine is known to cause G----A transitions during DNA replication in Escherichia coli, and its formation may be a carcinogenic event in higher organisms. To investigate the repair of N2,3-ethenoguanine, we have prepared an N2,3-etheno[14C]guanine-containing DNA substrate by nick-translating DNA with [14C]dGTP and modifying the product with chloroacetaldehyde. E. coli 3-methyladenine DNA glycosylase II, purified from cells which carry the plasmid pYN1000, releases N2,3-ethenoguanine from chloroacetaldehyde-modified DNA in a protein- and time-dependent manner. This finding widens the known substrate specificity of glycosylase II to include a modified base which may be associated with the carcinogenic process. Similar enzymatic activity in eukaryotic cell might protect them from exposure to metabolites of vinyl chloride. << Less
Proc Natl Acad Sci U S A 89:9331-9334(1992) [PubMed] [EuropePMC]