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Deoxyadenosine information


Deoxyadenosine
Skeletal formula of deoxyadenosine
Space-filling model of the deoxyadenosine molecule
Names
IUPAC name
(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Other names
2′-Deoxyadenosine; α-Deoxyadenosine; dA
Identifiers
CAS Number
  • 958-09-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17256 checkY
ChEMBL
  • ChEMBL416340 ☒N
ChemSpider
  • 13135 checkY
ECHA InfoCard 100.012.262 Edit this at Wikidata
IUPHAR/BPS
  • 5109
MeSH 2'-deoxyadenosine
PubChem CID
  • 636
UNII
  • P582C98ULC checkY
CompTox Dashboard (EPA)
  • DTXSID10883624 Edit this at Wikidata
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 checkY
    Key: OLXZPDWKRNYJJZ-RRKCRQDMSA-N checkY
  • InChI=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/s1
    Key: OLXZPDWKRNYJJZ-RRKCRQDMBK
SMILES
  • n2c1c(ncnc1n(c2)[C@@H]3O[C@@H]([C@@H](O)C3)CO)N
Properties
Chemical formula
C10H13N5O3
Molar mass 251.24192
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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).[1]

  1. ^ Griffiths, Anthony J. F.; Wessler, Susan R.; Carroll, Sean B.; Doebly, John (2012). Introduction to Genetic Analysis (10th ed.). New York: W . H. Freeman and Company. ISBN 978-1-4641-0661-3.

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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...

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Deoxyadenosine monophosphate

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Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is...

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Deoxyadenosine triphosphate

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Deoxyadenosine triphosphate (dATP) is a nucleotide used in cells for DNA synthesis (or replication), as a substrate of DNA polymerase. Deoxyadenosine...

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Deoxyadenosine diphosphate

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Deoxyadenosine diphosphate is a nucleoside diphosphate. It is related to the common nucleic acid ATP, or adenosine triphosphate, with the -OH (hydroxyl)...

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Cordycepin

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Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the replacement of the hydroxy group in the...

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Islatravir

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Islatravir (4′-ethynyl-2-fluoro-2′-deoxyadenosine, EFdA, or MK-8591) is an investigational drug for the treatment of HIV infection. It is classified as...

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Deoxyadenosine kinase

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In enzymology, a deoxyadenosine kinase (EC 2.7.1.76) is an enzyme that catalyzes the chemical reaction ATP + deoxyadenosine ⇌ {\displaystyle \rightleftharpoons...

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Adenine

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Adenosine is adenine reacted with ribose, as used in RNA and ATP; Deoxyadenosine is adenine attached to deoxyribose, as used to form DNA. Adenine forms...

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Adenosine

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one of the four nucleoside building blocks of RNA (and its derivative deoxyadenosine is a building block of DNA), which are essential for all life on Earth...

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Nucleotide

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called deoxyadenosine, whereas the whole structure along with the phosphate group is a nucleotide, a constituent of DNA with the name deoxyadenosine monophosphate...

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Lipid peroxidation

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mutagenic and carcinogenic. For instance, the end-product MDA reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts to them, primarily M1G...

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Nucleoside

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Deoxyribonucleoside adenine symbol A or Ade adenosine symbol A or Ado deoxyadenosine symbol dA or dAdo guanine symbol G or Gua guanosine symbol G or Guo...

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Malondialdehyde

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level of oxidative stress in an organism. Malondialdehyde reacts with deoxyadenosine and deoxyguanosine in DNA, forming DNA adducts, the primary one being...

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Tenofovir disoproxil

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disoproxil fumarate is converted to tenofovir, an acyclic analog of deoxyadenosine 5'-monophosphate (dAMP). Tenofovir lacks a hydroxyl group in the position...

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Purine

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corresponding nucleosides-deoxyribonucleosides (deoxyguanosine and deoxyadenosine) with deoxyribose moiety and ribonucleosides (guanosine, adenosine)...

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Thymidine

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deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize...

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Kinetin

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time, it was believed that kinetin was an artifact produced from the deoxyadenosine residues in DNA, which degraded when standing for long periods or when...

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Damp

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Deficits in Attention, Motor control and Perception, a psychiatric concept Deoxyadenosine monophosphate, or dAMP, a nucleic acid Digital AMPS, or D-AMPS, second-generation...

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Adenosine deaminase

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co-exists with ADA1. The two isoforms regulate the ratio of adenosine to deoxyadenosine potentiating the killing of parasites. ADA2 is found predominantly in...

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Methyl methanesulfonate

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treatment. MMS methylates DNA predominantly on N7-deoxyguanosine and N3-deoxyadenosine, and to a much lesser extent also methylates at other oxygen and nitrogen...

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Fluorinase

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co-factor S-adenosyl-L-methionine to generate L-methionine and 5'-fluoro-5'-deoxyadenosine, the first committed product of the fluorometabolite biosynthesis pathway...

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Cladribine

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B-cell leukaemia. Chemically, it mimics the nucleoside deoxyadenosine. However, unlike deoxyadenosine, it is relatively resistant to breakdown by the enzyme...

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Biphosphate

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any organic molecule with two phosphate groups Adenosine diphosphate Deoxyadenosine diphosphate Cytidine diphosphate Deoxycytidine diphosphate Guanosine...

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Adenosine deaminase deficiency

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adenosine deaminase. This deficiency results in an accumulation of deoxyadenosine, which, in turn, leads to: A buildup of dATP in all cells, which inhibits...

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