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8-Oxoguanine

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					8-Oxoguanine
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8-Oxoguanine (8-hydroxyguanine, 8-oxo-Gua, or OH 8 Gua) is one of the most
                                                                                                                  8-Oxoguanine[1]
common DNA lesions resulting from reactive oxygen species [2] and can result in
a mismatched pairing with Adenine resulting in G to T and A to C substitutions in
the genome. [3] In humans, it is primarily repaired by the DNA glycosylase OGG1.
It can be caused by ionizing radiation, in connection with oxidative metabolism.

                                                   References
                                          1. ^ 8-hydroxyguanine - Compound
                                                                                                                      IUPAC name
                                             Summary , PubChem
                                                                                                       2-Amino-7,9-dihydro-1H-purine-6,8-dione
                                          2. ^ S. Kanvah, et al., Oxidation of DNA:
                                             Damage to Nucleobases; Acc. Chem. Res.                                   Other names
                                             2010, 43(2), 280-287                                              8-Oxo-7,8-dihydroguanine
                                          3. ^ Cheng KC, Cahill DS, Kasai H, Nishimura
   8-oxoG (syn) in a Hoogsteen base pair                                                                                 Identifiers
                                             S, Loeb LA (1992 Jan 5). "8-
               with dA (anti)                                                                        CAS number                 5614-64-2
                                             Hydroxyguanine, an abundant form of
                                             oxidative DNA damage, causes G→T and                    PubChem                    119315
                                       A→C substitutions.". J Biol Chem. 267 (1): 166–72.            ChemSpider                 106574
                                       PMID 1730583 .                                                MeSH                       8-hydroxyguanine
                                                                                                     ChEBI                      CHEBI:44605
                                                                                                     Jmol-3D images             Image 1
                                                                                                                                Image 2
                                                                                                                          SMILES
                                                                                                     O=C2NC=1N\C(=N/C(=O)C=1N2)N

                                                                                                     c12=NC(=O)N=c1[nH]c(nc2=O)N
  For comparison here is a standard
                                                                                                                           InChI
 (non-mutagenic) GC base pair with
 both bases in the anti configuration                                                                InChI=1S/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-
   of the bond between base and                                                                      5(12)9-2/h(H3,6,8,9,10,11,12)
               sugar.                                                                                Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N

                                                                                                     InChI=1/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-
                                                                                                     5(12)9-2/h(H5,6,7,8,9,10,11,12)
                                                                                                     Key: CLGFIVUFZRGQRP-UHFFFAOYAZ

                                                                                                     InChI=1/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-
                                                                                                     5(12)9-2/h(H3,6,8,9,10,11,12)
                                                                                                     Key: UBKVUFQGVWHZIR-UHFFFAOYAW

                                                                                                                         Properties
                                                                                                     Molecular formula          C5 H5 N5 O 2
                                                                                                     Molar mass                 167.13 g mol−1
                                                                                                                   (verify) (what is:     / ?)
                                                                                                     Except where noted otherwise, data are given for
                                                                                                        materials in their standard state (at 25 °C,
                                                                                                                          100 kPa)
                                                                                                                    Infobox references

  V   · T· E·                                                       Nucleic acid constituents
                     Nucleobase         Purine (Adenine, Guanine, Purine analogue) · Pyrimidine (Uracil, Thymine, Cytosine, Pyrimidine analogue)

                                               Ribonucleoside    Adenosine · Guanosine · 5-Methyluridine · Uridine · Cytidine
                      Nucleoside
                                           Deoxyribonucleoside             Deoxyadenosine · Deoxyguanosine · Thymidine · Deoxyuridine · Deoxycytidine

                                                  Ribonucleotide           AMP, GMP, m 5 UMP, UMP, CMP
                      Nucleotide
                                           Deoxyribonucleotide             dAMP, dGMP, dTMP, dUMP, dCMP
 (Nucleoside monophosphate)
                                               Cyclic nucleotide           cAMP, cGMP, c-di-GMP, cADPR

     Nucleoside diphosphate              ADP, GDP, m 5 UDP, UDP, CDP · dADP, dGDP, dTDP, dUDP, dCDP

     Nucleoside triphosphate             ATP, GTP, m 5 UTP, UTP, CTP · dATP, dGTP, dTTP, dUTP, dCTP
      biochemical families: proteins (amino acids /intermediates ) · nucleic acids (constituents /intermediates ) · carbohydrates (glycoproteins , alcohols , glycosides )

                             lipids (fatty acids /intermediates , phospholipids , steroids, sphingolipids , eicosanoids) · tetrapyrroles /intermediates




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posted:9/13/2012
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