Deoxyadenosine triphosphate

Deoxyadenosine triphosphate
Skeletal formula of deoxyadenosine triphosphate
Ball-and-stick model of the deoxyadenosine triphosphate anion
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 Edit this at Wikidata
  • 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 checkY=  checkY
    Key: SUYVUBYJARFZHO-RRKCRQDMSA-N checkY=  checkY
  • 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).
checkY verify (what is checkY☒N ?)

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

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

  1. ^ Romaniuk PJ, Eckstein F (July 1982). "A study of the mechanism of T4 DNA polymerase with diastereomeric phosphorothioate analogues of deoxyadenosine triphosphate". The Journal of Biological Chemistry. 257 (13): 7684–7688. doi:10.1016/S0021-9258(18)34435-1. PMID 7045112.
  2. ^ Ladner WE, Whitesides GM (1985-04-01). "Enzymic synthesis of deoxyATP using DNA as starting material". The Journal of Organic Chemistry. 50 (7): 1076–1079. doi:10.1021/jo00207a032. ISSN 0022-3263.
  3. ^ Chang CH, Cheng YC (October 1980). "Effects of deoxyadenosine triphosphate and 9-beta-D-arabinofuranosyl-adenine 5'-triphosphate on human ribonucleotide reductase from Molt-4F cells and the concept of "self-potentiation"". Cancer Research. 40 (10): 3555–3558. PMID 6159965.
  4. ^ Cohen A, Hirschhorn R, Horowitz SD, Rubinstein A, Polmar SH, Hong R, Martin DW (January 1978). "Deoxyadenosine triphosphate as a potentially toxic metabolite in adenosine deaminase deficiency". Proceedings of the National Academy of Sciences of the United States of America. 75 (1): 472–476. Bibcode:1978PNAS...75..472C. doi:10.1073/pnas.75.1.472. PMC 411272. PMID 272665.
  5. ^ Sanchez JJ, Monaghan G, Børsting C, Norbury G, Morling N, Gaspar HB (May 2007). "Carrier frequency of a nonsense mutation in the adenosine deaminase (ADA) gene implies a high incidence of ADA-deficient severe combined immunodeficiency (SCID) in Somalia and a single, common haplotype indicates common ancestry". Annals of Human Genetics. 71 (Pt 3): 336–347. doi:10.1111/j.1469-1809.2006.00338.x. PMID 17181544. S2CID 34850391.
  6. ^ Cheng Y, Hogarth KA, O'Sullivan ML, Regnier M, Pyle WG (January 2016). "2-Deoxyadenosine triphosphate restores the contractile function of cardiac myofibril from adult dogs with naturally occurring dilated cardiomyopathy". American Journal of Physiology. Heart and Circulatory Physiology. 310 (1): H80 – H91. doi:10.1152/ajpheart.00530.2015. PMC 4796460. PMID 26497964.
  7. ^ Powers JD, Yuan CC, McCabe KJ, Murray JD, Childers MC, Flint GV, et al. (June 2019). "Cardiac myosin activation with 2-deoxy-ATP via increased electrostatic interactions with actin". Proceedings of the National Academy of Sciences of the United States of America. 116 (23): 11502–11507. Bibcode:2019PNAS..11611502P. doi:10.1073/pnas.1905028116. PMC 6561254. PMID 31110001.

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