13875-63-3

Basic information

• Product Name: 1,N6-ETHENOADENINE
• Synonyms: 1,N6-ETHENOADENINE;1,N(sup 6)-ethenoadenine;1H-Imidazo[2,1-i]purine;3H-Imidazo[2,1-i]purine;6H-1,3a,5,6,8-Pentaaza-as-indacene;N,1-Vinylene-9H-purine-6(1H)-imine;N6-Ethenoadenine
• CAS NO: 13875-63-3
• Molecular Formula: C₇H₅N₅
• Molecular Weight: 159.15
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 13875-63-3.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.78g/cm³
• Refractive Index: 1.956
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,N6-ETHENOADENINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,N6-ETHENOADENINE(13875-63-3)
• EPA Substance Registry System: 1,N6-ETHENOADENINE(13875-63-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13875-63-3(Hazardous Substances Data)

Usage

Uses

1,N6-Ethenoadenine is a mutagenic DNA lesion.

InChI:InChI=1/C7H5N5/c1-2-12-4-11-6-5(7(12)8-1)9-3-10-6/h1-4H,(H,9,10)

Upstream product

• 68498-25-9 3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine 
• 107-20-0 2-chloroethanal 
• 73-24-5 7H-purin-6-ylamine 

Downstream Products

• 68498-25-9 3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine 

Relevant articles and documents

N-glycosyl bond formation catalyzed by human alkyladenine DNA glycosylase

The removal of damaged bases by DNA glycosylases is thought to be effectively irreversible, because of an overall equilibrium that favors hydrolysis over synthesis of the N-glycosyl bond. Surprisingly, human alkyladenine DNA glycosylase (AAG) can make damaged DNA by catalyzing formation of an N-glycosyl bond between 1,N6-ethenoadenine (εA) and abasic DNA. We attribute the ready reversibility of this glycosylase reaction to the exceptionally tight binding and slow subsequent hydrolysis of DNA containing an εA lesion. In principle, reversibility could provide a mechanism for direct reversal of base damage by a DNA glycosylase, allowing the glycosylase to bypass the rest of the base excision repair pathway.

A New One-Pot Fluorescence Derivatization Strategy for Highly Sensitive MicroRNA Analysis

MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one-pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N6-ethenoadenine (?-adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2-chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ?-adenine and water-mediated hydrogen-bond interaction between the proton at the 2′- and the oxyanion at 3′-positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high-performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid-phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub-picomolar level in serum samples.