DNAmod: N2-carboxyethylguanine

Description

An alanine derivative consisting of alanine having a 6-oxo-6,9-dihydro-1H-purin-2-yl group attached to the amino function.

Chemical properties

Chemical formula	Net charge	Average mass
C8H9N5O3	0	223.18880

<i>N</i><sup>2</sup>-carboxyethylguanine

Recommended notation

Name	N²-carboxyethylguanine
Abbreviation	CEG

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
N-(6-oxo-6,9-dihydro-1H-purin-2-yl)alanine	CC(Nc1nc2[nH]cnc2c(=O)[nH]1)C(O)=O	InChI=1S/C8H9N5O3/c1-3(7(15)16)11-8-12-5-4(6(14)13-8)9-2-10-5/h2-3H,1H3,(H,15,16)(H3,9,10,11,12,13,14)	YCCGSWHBNBAHIT-UHFFFAOYSA-N	n(2)-(1-carboxyethyl)guanine ceguanine

Nature

Origin	Function	Functional detail	Organisms	References
natural	damage	mutagenic	Homo sapiens	Schneider, M, et al. 2004. Determination of glycated nucleobases in human urine by a new monoclonal antibody specific for N2-carboxyethyl-2'-deoxyguanosine. Chemical Research in Toxicology. 17(10).

Database references:

CHEBI:62032

Citations

Schneider, M, et al. 2004. Determination of glycated nucleobases in human urine by a new monoclonal antibody specific for N2-carboxyethyl-2'-deoxyguanosine. Chemical Research in Toxicology. 17(10).
Schneider, M, et al. 2006. Detection of DNA-bound advanced glycation end-products by immunoaffinity chromatography coupled to HPLC-diode array detection. Molecular Nutrition & Food Research. 50(4-5).
Seidel, W, et al. 1998. DNA-glycation leads to depurination by the loss of N2-carboxyethylguanine in vitro. Cellular and Molecular Biology (Noisy-le-Grand, France). 44(7).