Deoxyadenosine

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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.

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IUPAC name
(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Other names
2′-Deoxyadenosine; α-Deoxyadenosine; dA
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}958-09-8 Y
3D model (JSmol)Interactive image
ChEBICHEBI:17256 Y
ChEMBLChEMBL416340 N
ChemSpider13135 Y
ECHA InfoCard100.012.262
IUPHAR/BPS5109
MeSH2'-deoxyadenosine
PubChem CID636
UNIIP582C98ULC Y
CompTox Dashboard (EPA)DTXSID10883624
InChI
InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1 YKey: OLXZPDWKRNYJJZ-RRKCRQDMSA-N YInChI=1/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1Key: OLXZPDWKRNYJJZ-RRKCRQDMBK
SMILES
n2c1c(ncnc1n(c2)[C@@H]3OC@@HCO)N
Chemical formulaC10H13N5O3
Molar mass251.24192
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Infobox 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).

  • Deoxyribonucleotide
  • Cordycepin (3′-deoxyadenosine)
  • Severe combined immunodeficiency

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