1,N⁶-Ethanoadenine

1,N⁶-Ethanoadenine
Names
	IUPAC name 8,9-dihydro-7H-imidazo[2,1-f]purine
Identifiers
CAS Number	91996-61-1;
3D model (JSmol)	Interactive image;
ChemSpider	61297663;
MeSH	1,N(6)-ethanoadenine
PubChem CID	136138644;
	InChI 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;
	SMILES C1CN2C=NC3=NC=NC3=C2N1;
Properties
Chemical formula	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). Infobox references

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

^ ^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.
^ 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.
^ 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.

[mac-1] 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.

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