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]
Structure of the deoxyadenosyl radical
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Names | |
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IUPAC name
5′-Deoxyadenosin-5′-yl
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Systematic IUPAC name
[(2R,3R,4S,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl | |
Identifiers | |
3D model (JSmol)
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PubChem CID
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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).
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References
edit- ^ 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.