Deoxyadenosyl radical

5′-Deoxyadenosyl radical
	; Structure of the deoxyadenosyl radical
Names
	IUPAC name 5′-Deoxyadenosin-5′-yl
	Systematic IUPAC name [(2R,3R,4S,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	5459908;
	InChI InChI=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 Key: FMJPFPZKXLRBOJ-KQYNXXCUSA-N;
	SMILES [CH2]C1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O;
Properties
Chemical formula	C10H12N5O3
Molar mass	250.238 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1] The deoxyadenosyl radical abstracts hydrogen atoms from substrates, causing rearrangements and other post transcriptional modifications required for biosynthesis.^[2]

References

^ Jennifer Bridwell-Rabb; Tsehai A. J. Grell; Catherine L. Drennan (2018). "A Rich Man, Poor Man Story of S-Adenosylmethionine and Cobalamin Revisited". Annual Review of Biochemistry. 87: 555–84. doi:10.1146/annurev-biochem-062917-012500. PMID 29925255. S2CID 49354135.
^ Broderick, J. B.; Duffus, B. R.; Duschene, K. S.; Shepard, E. M. (2014). "Radical S-Adenosylmethionine Enzymes". Chemical Reviews. 114 (8): 4229–4317. doi:10.1021/cr4004709. PMC 4002137. PMID 24476342.

[1] Jennifer Bridwell-Rabb; Tsehai A. J. Grell; Catherine L. Drennan (2018). "A Rich Man, Poor Man Story of S-Adenosylmethionine and Cobalamin Revisited". Annual Review of Biochemistry. 87: 555–84. doi:10.1146/annurev-biochem-062917-012500. PMID 29925255. S2CID 49354135.

[2] Broderick, J. B.; Duffus, B. R.; Duschene, K. S.; Shepard, E. M. (2014). "Radical S-Adenosylmethionine Enzymes". Chemical Reviews. 114 (8): 4229–4317. doi:10.1021/cr4004709. PMC 4002137. PMID 24476342.

[1]

[2]

Names
Structure of the deoxyadenosyl radical
IUPAC name 5′-Deoxyadenosin-5′-yl
Systematic IUPAC name [(2R,3R,4S,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	5459908
InChI InChI=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 Key: FMJPFPZKXLRBOJ-KQYNXXCUSA-N
SMILES [CH2]C1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
Properties
Chemical formula	C₁₀H₁₂N₅O₃
Molar mass	250.238 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references