Movatterモバイル変換

Deoxyadenosine

From Wikipedia, the free encyclopedia

Deoxyadenosine
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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17256^Y
ChEMBL	ChEMBL416340^N
ChemSpider	13135^Y
ECHA InfoCard	100.012.262
IUPHAR/BPS	5109
MeSH	2'-deoxyadenosine
PubChem CID	636
UNII	P582C98ULC^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^Y Key: OLXZPDWKRNYJJZ-RRKCRQDMSA-N^Y 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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Deoxyadenosine (symboldA ordAdo) is adeoxyribonucleoside. It is aderivative of thenucleoside adenosine, differing from the latter by the replacement of ahydroxyl group (-OH) by hydrogen (-H) at the2′ position of itsribose sugarmoiety. Deoxyadenosine is the DNA nucleoside A, which pairs withdeoxythymidine (T) in double-stranded DNA.

In absence ofadenosine 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]

References

[edit]

This articleneeds additional citations forverification. Please helpimprove this article byadding citations to reliable sources. Unsourced material may be challenged and removed.
Find sources: "Deoxyadenosine" – news ·newspapers ·books ·scholar ·JSTOR(January 2013) (Learn how and when to remove this message)

^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.

Nucleic acid constituents

Nucleobase

Nucleoside

Ribonucleoside	Adenosine Guanosine 5-Methyluridine Uridine 5-Methylcytidine Cytidine Pseudouridine Inosine N⁶-Methyladenosine Xanthosine Wybutosine
Deoxyribonucleoside	Deoxyadenosine Deoxyguanosine Thymidine Deoxyuridine Deoxycytidine Deoxyinosine Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide	AMP GMP m⁵UMP UMP CMP IMP XMP
Deoxyribonucleotide	dAMP dGMP dTMP dUMP dCMP dIMP dXMP
Cyclic nucleotide	cAMP cGMP c-di-GMP c-di-AMP cADPR cGAMP