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Deoxyadenosine triphosphate

Chemical compound From Wikipedia, the free encyclopedia

Deoxyadenosine triphosphate

Deoxyadenosine triphosphate (dATP) is a nucleotide used in cells for DNA synthesis (or replication), as a substrate of DNA polymerase.[1]

Quick Facts Names, Identifiers ...
Deoxyadenosine triphosphate
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Names
IUPAC name
[[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Other names
dATP, 2'-deoxyadenosine triphosphate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.058
  • InChI=1S/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 Y=  Y
    Key: SUYVUBYJARFZHO-RRKCRQDMSA-N Y=  Y
  • InChI=1/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
    Key: SUYVUBYJARFZHO-RRKCRQDMBD
  • O=P(O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)C[C@@H]3O
Properties
C10H16N5O12P3
Molar mass 491.181623
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Deoxyadenosine triphosphate is produced from DNA by the action of nuclease P1, adenylate kinase, and pyruvate kinase.[2]

Health effects

High levels of dATP can be toxic and result in impaired immune function, since dATP acts as a noncompetitive inhibitor for the DNA synthesis enzyme ribonucleotide reductase. Patients with adenosine deaminase deficiency (ADA) tend to have elevated intracellular dATP concentrations because adenosine deaminase normally curbs adenosine levels by converting it into inosine.[3][4] Deficiency of this deaminase also causes immunodeficiency.[5]

In cardiac myosin, dATP is an alternative to ATP as an energy substrate for facilitating cross-bridge formation.[6][7]

See also

References

Further reading

External links

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