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1,N6-Ethanoadenine

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1,N6-Ethanoadenine
Names
IUPAC name
8,9-dihydro-7H-imidazo[2,1-f]purine
Identifiers
3D model (JSmol)
ChemSpider
MeSH 1,N(6)-ethanoadenine
  • InChI=1S/C7H7N5/c1-2-12-4-11-6-5(7(12)8-1)9-3-10-6/h3-4,8H,1-2H2
    Key: NTUVVWKLOXHUNZ-UHFFFAOYSA-N
  • C1CN2C=NC3=NC=NC3=C2N1
Properties
C7H7N5
Molar mass 161.168 g·mol−1
Related compounds
Related compounds
3,N4-Ethenocytosine; 1,N6-Ethenoadenine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,N6-Ethanoadenine or epsilonA is a tricyclic derivative of adenine, where an ethylene bridge connect the amine group to the adjacent carbon on the six member ring, to add another five membered ring. This kind of modification can take place as a mutation of DNA. As a DNA modification it is called an etheno (ε) DNA adduct.[1] Chloroacetaldehyde[1] and 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) can react with adenine to form 1,N6-ethanoadenine.[2]

Escherichia coli can fix these modifications using AlkB protein.[1]

Another way to produce it is via cyclisation of N6-hydroxyethyladenine with DIAD and triphenylphosphine in the Mitsunobu reaction in a THF/MeCN solvent or by reacting with SOCl2.[3]

References

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  1. ^ a b c MacIejewska, A. M.; Sokolowska, B.; Nowicki, A.; Kusmierek, J. T. (2011). "The role of AlkB protein in repair of 1,N6-ethenoadenine in Escherichia coli cells". Mutagenesis. 26 (3): 401–406. doi:10.1093/mutage/geq107. PMID 21193516.
  2. ^ Hang, B (29 October 2003). "Miscoding properties of 1,N6-ethanoadenine, a DNA adduct derived from reaction with the antitumor agent 1,3-bis(2-chloroethyl)-1-nitrosourea". Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 531 (1–2): 191–203. doi:10.1016/j.mrfmmm.2003.07.006. PMID 14637255. S2CID 32641844.
  3. ^ Šimůnková, Naděžda; Tobrman, Tomáš; Eigner, Václav; Dvořák, Dalimil (November 2017). "A Study on the Intramolecular Mitsunobu Reaction of N6-(ω-Hydroxyalkyl)adenines". Journal of Heterocyclic Chemistry. 54 (6): 3565–3573. doi:10.1002/jhet.2982.