Chemistry:Deoxyadenosyl radical

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5′-Deoxyadenosyl radical
Deoxyadenosyl radical.svg
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)
Properties
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

  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. 
  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. PMID 24476342.