Deoxyadenosine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460775595

|ImageFile=Desoxyadenosin.svg

|ImageSize=160px

|ImageAlt = Skeletal formula of deoxyadenosine

|ImageFile1 = Deoxyadenosine-3D-spacefill.png

|ImageSize1 = 180

|ImageAlt1 = Space-filling model of the deoxyadenosine molecule

|IUPACName = (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

|OtherNames = 2′-Deoxyadenosine; α-Deoxyadenosine; dA

|Section1= {{Chembox Identifiers

| IUPHAR_ligand = 5109

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 13135

| 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

| InChIKey = OLXZPDWKRNYJJZ-RRKCRQDMBK

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OLXZPDWKRNYJJZ-RRKCRQDMSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=958-09-8

| PubChem=636

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 416340

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = P582C98ULC

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17256

| SMILES = n2c1c(ncnc1n(c2)[C@@H]3O[C@@H]([C@@H](O)C3)CO)N

| MeSHName=2'-deoxyadenosine

}}

|Section2= {{Chembox Properties

| Formula=C₁₀H₁₃N₅O₃

| MolarMass=251.24192

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

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|Section3= {{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt=

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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 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).{{cite book |last1=Griffiths |first1=Anthony J. F. |last2=Wessler |first2=Susan R. |last3=Carroll |first3=Sean B. |last4=Doebly |first4=John |year=2012 |title=Introduction to Genetic Analysis |edition=10th |publication-place=New York |publisher=W . H. Freeman and Company |isbn=978-1-4641-0661-3}}