deoxyadenosyl radical
{{Chembox
| Name = 5′-Deoxyadenosyl radical
| ImageFile = Deoxyadenosyl radical.svg
| ImageCaption = Structure of the deoxyadenosyl radical
| IUPACName = 5′-Deoxyadenosin-5′-yl
| SystematicName = [(2R,3R,4S,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl
|Section1={{Chembox Identifiers
| PubChem = 5459908
| StdInChI=1S/C10H12N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
| StdInChIKey = FMJPFPZKXLRBOJ-KQYNXXCUSA-N
| SMILES = [CH2]C1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
}}
|Section2={{Chembox Properties
| C=10|H=12|N=5|O=3
}}
}}
A deoxyadenosyl radical is a free radical that is structurally related to adenosine by removal of a 5′-hydroxy group from adenosine. This radical occurs in nature as a reactive intermediate. It is generated by radical SAM enzymes and by some varieties of vitamin B12.{{cite journal|year=2018|journal=Annual Review of Biochemistry|title=A Rich Man, Poor Man Story of S-Adenosylmethionine and Cobalamin Revisited|author=Jennifer Bridwell-Rabb |author2=Tsehai A. J. Grell |author3=Catherine L. Drennan |volume=87|pages=555–84|doi=10.1146/annurev-biochem-062917-012500|pmid=29925255|s2cid=49354135 }} The deoxyadenosyl radical abstracts hydrogen atoms from substrates, causing rearrangements and other post transcriptional modifications required for biosynthesis.{{cite journal|author1=Broderick, J. B. |author2=Duffus, B. R. |author3=Duschene, K. S. |author4=Shepard, E. M. |title=Radical S-Adenosylmethionine Enzymes|journal=Chemical Reviews|year=2014|volume=114|issue=8|pages=4229–4317|doi= 10.1021/cr4004709|pmid=24476342|pmc=4002137}}