Deoxyguanosine

Deoxyguanosine[1]
Skeletal formula of deoxyadenosine
Ball-and-stick model of the deoxyadenosine molecule
Names
IUPAC name
2-Amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.278
MeSH Deoxyguanosine
UNII
  • InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1 checkY
    Key: YKBGVTZYEHREMT-KVQBGUIXSA-N checkY
  • InChI=1/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1
    Key: YKBGVTZYEHREMT-KVQBGUIXBI
  • c1nc2c(n1[C@H]3C[C@@H]([C@H](O3)CO)O)[nH]c(nc2=O)N
Properties
C10H13N5O4
Molar mass 267.245 g·mol−1
Melting point 250 °C (482 °F; 523 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)
Infobox references

Deoxyguanosine (dG) is composed of the purine nucleobase guanine linked by its N9 nitrogen to the C1 carbon of deoxyribose. It is similar to guanosine, but with one hydroxyl group removed from the 2' position of the ribose sugar (making it deoxyribose). If a phosphate group is attached at the 5' position, it becomes deoxyguanosine monophosphate.

Deoxyguanosine is one of the four deoxyribonucleosides that make up DNA.[2]

Potential Damage to Deoxyguanosine

Deoxyguanosine is a base that is vulnerable to reactive oxygen species (ROS) because of its comparatively lower oxidation potential. As a result, ROS can oxidize dG to make 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG). This modification is known as a pre-mutagenic lesion, meaning that the damage can still be repaired, but can lead to a mutation if left alone. The oxidation of dG can be detrimental to the genome since 8-oxodG base pairs with deoxyadenosine (dA) instead of the deoxycytidine (dC), which is the proper Watson-Crick base pair. Consequently, if the lesion is not repaired via the mismatch repair mechanism, during DNA replication a dA will take the place of the dC, resulting in a mutation.[3]

Deoxyguanosine is also a base that is prone to reacting with carcinogens, such as polyaromatic hydrocarbons (PAHs). Once the PAHs are metabolized and made stable in the intracellular environment, they can react with dG to form 7-methyldeoxyguanosine or O6-methyldeoxyguanosine. The presence of these modifications can then lead to downstream effects that lower the fidelity of DNA replication and potentially cause mutations.[4]

See also

References

  1. ↑ "2'-deoxyguanosine". PubChem Compound Database. National Center for Biotechnology Information. 24 December 2016. Archived from the original on 2 January 2017. Retrieved 2 January 2017.
  2. ↑ "Human Metabolome Database (HMDB) metabocard for Deoxyguanosine (HMDB0000085)".
  3. ↑ Gorini, Francesca; Scala, Giovanni; Cooke, Marcus S.; Majello, Barbara; Amente, Stefano (2021-01-01). "Towards a comprehensive view of 8-oxo-7,8-dihydro-2'-deoxyguanosine: Highlighting the intertwined roles of DNA damage and epigenetics in genomic instability". DNA Repair. 97 103027. doi:10.1016/j.dnarep.2020.103027. ISSN 1568-7864. PMC 7926032. PMID 33285475.
  4. ↑ Peterson, L.A.; Urban, A.M.; Hecht, S.S. (2010-01-01). "Carcinogenic Effects of Cigarette Smoke on the Respiratory Tract". Comprehensive Toxicology (Second Edition): 351–377. doi:10.1016/B978-0-08-046884-6.00919-2.
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