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Deoxyadenosyl radical information


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]

  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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Deoxyadenosyl radical

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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...

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Radical SAM

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(SAM) to generate a radical, usually a 5′-deoxyadenosyl radical (5'-dAdo), as a critical intermediate. These enzymes utilize this radical intermediate to...

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Adenosylcobalamin

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a cofactor in radical-mediated 1,2-carbon skeleton rearrangements. These processes require the formation of the deoxyadenosyl radical through homolytic...

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Ribonucleotide reductase

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a radical generated with the stabilization of a binuclear manganese center. Class II reductases generate the free radical 5’-deoxyadenosyl radical from...

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Vitamin B12

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chemistry of vitamin B12, allowing it to serve as a donor of deoxyadenosyl radical (radical alkyl source) and as a methyl cation equivalent (electrophilic...

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Biotin synthase

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generating a 5’-deoxyadenosyl radical (5’-dA). This carbon radical abstracts a hydrogen from dethiobiotin, forming a dethiobiotinyl C9 carbon radical, which is...

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Spore photoproduct lyase

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which cleaves a part of the structure and forms a 5'-deoxyadenosyl radical. This 5'-deoxyadenosyl radical will then remove a hydrogen atom from the substrate...

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Lipoyl synthase

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is used by this enzyme to produce 5'-deoxyadenosyl 5'-radical (5'-dA). Lipoyl synthase itself uses this radical to abstract hydrogens from the 6th and...

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Methylthiotransferase

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otherwise known as radical SAM enzymes, are metalloproteins that cleave S-adenosyl-L-methionine into L-methionine and a 5'-deoxyadenosyl 5'-radical (5'-dA). 5'-dA...

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