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Deoxyadenosyl radical

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5′-Deoxyadenosyl radical

Structure of the deoxyadenosyl radical
Names
IUPAC name 5′-Deoxyadenosin-5′-yl
Systematic IUPAC name methyl
Identifiers
3D model (JSmol)
PubChem CID
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/s1Key: FMJPFPZKXLRBOJ-KQYNXXCUSA-N
SMILES
  • C1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
Properties
Chemical formula C10H12N5O3
Molar mass 250.238 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

References

  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.
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