Structure via PubChem · Public domain (PubChem)
2'-deoxyadenosine
Sign in to saveAlso known as 9-(2-deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine, (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol, adenyldeoxyriboside, 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine, adenine deoxyribonucleoside, 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine, Desoxyadenosine, 2-Deoxyadenosine
Deoxyadenosine (symbol dA or dAdo) is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2′ position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA.
Chemical data
- Formula
- C10H13N5O3
- Molecular weight
- 251.24 g/mol
- IUPAC name
- (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
- SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O
- InChIKey
- OLXZPDWKRNYJJZ-RRKCRQDMSA-N
- XLogP
- -0.5
- Polar surface area
- 119 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
2,686 papers- 2-Chloro-2'-deoxyadenosine.Acta clinica Belgica · 1995
- Characterization of 2-Fluoro-2'-deoxyadenosine in Duplex, G-Quadruplex and i-Motif.Chembiochem : a European journal of chemical biology · 2022
- N(6)-Deoxyadenosine Methylation in Mammalian Mitochondrial DNA.Molecular cell · 2020
- 2-chloro-2'-deoxyadenosine: clinical applications in hematology.Blood reviews · 1996
- Synthesis of 2'-deoxyguanosine from 2'-deoxyadenosine via C2 nitration.Nucleosides, nucleotides & nucleic acids · 2022
via PubMed
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Encyclopedic overview
2 sectionsContents
- See also
- References
Deoxyadenosine (symbol dA or dAdo) is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2′ position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA.
In absence of adenosine deaminase (ADA) it accumulates in T lymphocytes and kills these cells resulting in a genetic disorder known as adenosine deaminase severe combined immunodeficiency disease (ADA-SCID).
Excerpted from Wikipedia’s “2'-deoxyadenosine” article, available under the CC BY-SA 4.0 licence.