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Deoxyadenosine triphosphate

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(Redirected fromDATP)
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 InfoCard100.016.058Edit 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 mass491.181623
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Deoxyadenosine triphosphate (dATP) is anucleotide used in cells forDNA synthesis (or replication), as a substrate ofDNA polymerase.[1]

Deoxyadenosine triphosphate is produced fromDNA by the action ofnuclease P1,adenylate kinase, andpyruvate kinase.[2]

Health effects

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High levels of dATP can betoxic and result in impairedimmune function, since dATP acts as anoncompetitive inhibitor for the DNA synthesisenzymeribonucleotide reductase. Patients withadenosine deaminase deficiency (ADA) tend to have elevatedintracellular dATP concentrations becauseadenosine deaminase normally curbsadenosine levels by converting it intoinosine.[3][4] Deficiency of this deaminase also causes immunodeficiency.[5]

Incardiacmyosin, dATP is an alternative to ATP as an energy substrate for facilitatingcross-bridge formation.[6][7]

See also

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References

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  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.

Further reading

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External links

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Nucleic acid constituents
Nucleobase
Nucleoside
Ribonucleoside
Deoxyribonucleoside
Nucleotide
(Nucleoside monophosphate)
Ribonucleotide
Deoxyribonucleotide
Cyclic nucleotide
Nucleoside diphosphate
Nucleoside triphosphate
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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