n6-Ethenoadenine

• CAS: 13875-63-3
• Catalog Number: ACM13875633
• Category: Main Products
• Molecular Weight: 159.15
• Molecular Formula: C₇H₅N₅

Case Study

Base Recognition Properties of RNA Oligonucleotides Containing 1,N6-Ethenoadenine and 3,N4 -Ethenocytosine

Calabretta, Alessandro, et al. Biochemistry, 2013, 52(11), 1990-1997.

This work reports the synthesis of short 12-mer oligonucleotides containing a single 1,N6-ethenoadenine (εA) or 3,N4-ethenocytosine (εC) nucleotide and their base recognition properties when duplex formation with complementary DNA and RNA.
The melting temperature (Tm) data for the duplexes featuring etheno modifications opposite all natural bases indicated a significant destabilization compared to the corresponding natural duplexes, which supports the notion that these modifications cannot effectively form base pairs.
To further explore the coding properties of these lesions, they were introduced into 31-mer oligonucleotides, and their capability to function as templates in primer extension reactions with HIV, AMV, and MMLV reverse transcriptases (RT) was evaluated. The results of the primer extension reactions revealed that MMLV RT and AMV RT completely halted the incorporation process, while HIV RT exhibited a preference for incorporating dAMP opposite εA and both dAMP and dTMP opposite εC. The characteristics of these RNA lesions are examined in relation to their potential biological significance.

1,N6-Ethenoadenine Forms Ag(I)-Mediated Base Pair with Thymine

Mandal, Soham,et al. Inorganica Chimica Acta, 2018, 472, 229-233.

Early studies on 1,N6-ethenoadenine (εA) showed that εA has superior metal binding ability compared with standard nucleobases, suggesting that εA may be a good candidate for metal-mediated base pairing. This work investigates the suitability of εA in metal-mediated base pairing. Specifically, the artificial nucleobase εA can form binuclear Ag(I)-mediated base pairs with complementary thymine (T) residues in duplex DNA.
The formation of a metal-mediated base pair significantly stabilizes the duplex, increasing its thermal stability by 5-6 °C. This stabilizing effect remains consistent regardless of the base pair's orientation within the duplex; both εA-Ag(I)2-T and T-Ag(I)2-εA configurations exhibit equal stability. Circular dichroism and temperature-dependent UV spectroscopy confirmed the formation of this Ag(I)-mediated base pair.
DFT calculations suggest a base pair configuration where one Ag(I) ion coordinates with εA-N6 and T-O4, while the other Ag(I) ion forms coordinate bonds with εA-N7 and T-N3. The calculations indicate a short intramolecular Ag···Ag distance of 2.87 Å, suggesting the potential involvement of argentophilic interactions.

Custom Q&A

What is the molecular formula of n6-Ethenoadenine?

The molecular formula of n6-Ethenoadenine is C44H55NO16.

What are the synonyms for n6-Ethenoadenine?

Some synonyms for n6-Ethenoadenine include 138777-25-0, C12FDG, and 5-Dodecanoylaminoflorescein di-b-D-galactopyranoside.

When was n6-Ethenoadenine created?

n6-Ethenoadenine was created on December 4, 2007.

What is the molecular weight of n6-Ethenoadenine?

The molecular weight of n6-Ethenoadenine is 853.9 g/mol.

What is the IUPAC name of n6-Ethenoadenine?

The IUPAC name of n6-Ethenoadenine is N-[3-oxo-3',6'-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]spiro[2-benzofuran-1,9'-xanthene]-5-yl]dodecanamide.

What is the InChI of n6-Ethenoadenine?

The InChI of n6-Ethenoadenine is InChI=1S/C44H55NO16/c1-2-3-4-5-6-7-8-9-10-11-34(48)45-23-12-15-27-26(18-23)41(55)61-44(27)28-16-13-24(56-42-39(53)37(51)35(49)32(21-46)59-42)19-30(28)58-31-20-25(14-17-29(31)44)57-43-40(54)38(52)36(50)33(22-47)60-43/h12-20,32-33,35-40,42-43,46-47,49-54H,2-11,21-22H2,1H3,(H,45,48)/t32-,33-,35+,36+,37+,38+,39-,40-,42-,43-/m1/s1.

What is the InChIKey of n6-Ethenoadenine?

The InChIKey of n6-Ethenoadenine is SLIWIQKBDGZFQR-PIVCGYGYSA-N.

What is the Canonical SMILES of n6-Ethenoadenine?

The Canonical SMILES of n6-Ethenoadenine is CCCCCCCCCCCC(=O)NC1=CC2=C(C=C1)C3(C4=C(C=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC6=C3C=CC(=C6)OC7C(C(C(C(O7)CO)O)O)O)OC2=O.

What is the CAS number of n6-Ethenoadenine?

The CAS number of n6-Ethenoadenine is 138777-25-0.

What is the XLogP3-AA value of n6-Ethenoadenine?

The XLogP3-AA value of n6-Ethenoadenine is 4.2.