2140-77-4

Basic information

• Product Name: N2-METHYLGUANOSINE
• Synonyms: N2-METHYLGUANOSINE;2-Methylguanosine;9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-methylamino-3H-purin-6-one;N-Methylguanosine;Guanosine, N-methyl-;m2G
• CAS NO: 2140-77-4
• Molecular Formula: C11H15N5O5
• Molecular Weight: 297.27
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 2140-77-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 233 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 709.5°Cat760mmHg
• Flash Point: 382.9°C
• Appearance: /
• Density: 2g/cm³
• Vapor Pressure: 3.99E-21mmHg at 25°C
• Refractive Index: 1.849
• Storage Temp.: −20°C
• PKA: 9.87±0.20(Predicted)
• CAS DataBase Reference: N2-METHYLGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N2-METHYLGUANOSINE(2140-77-4)
• EPA Substance Registry System: N2-METHYLGUANOSINE(2140-77-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2140-77-4(Hazardous Substances Data)

Usage

Description

N2-METHYLGUANOSINE, also known as 2-methylguanosine, is a modified nucleoside derived from guanosine with a methyl group attached to the amine at the N-2 position. This modification can have significant effects on the structure and function of RNA molecules, making it an important molecule in the study of RNA biology and its potential applications.

Uses

Used in Pharmaceutical Industry:
N2-METHYLGUANOSINE is used as a therapeutic agent for its potential role in modulating RNA function and stability. The methylation of guanosine can influence the activity of various RNA molecules, making it a promising candidate for the development of drugs targeting specific RNA-based diseases.
Used in Research Applications:
N2-METHYLGUANOSINE is used as a research tool for studying the role of RNA methylation in various biological processes. It can help researchers understand the mechanisms by which RNA methylation affects gene expression, regulation, and cellular function.
Used in Drug Development:
N2-METHYLGUANOSINE is used as a lead compound in the development of new drugs targeting RNA-based diseases. Its unique structure and potential effects on RNA function make it an attractive target for the design of novel therapeutic agents.
Used in Diagnostic Applications:
N2-METHYLGUANOSINE can be used as a biomarker for certain diseases, particularly those involving alterations in RNA methylation patterns. Detecting changes in the levels of N2-METHYLGUANOSINE may help in the diagnosis and monitoring of these diseases.

InChI:InChI=1/C11H15N5O5/c1-12-11-14-8-5(9(20)15-11)13-3-16(8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15,20)/t4-,6-,7-,10-/m1/s1

Upstream product

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• 74-89-5 methylamine 
• 684-93-5 1-methyl-1-nitrosourea 
• 118-00-3 G 
• 73196-82-4 9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(((p-tolylthio)methyl)amino)-1,9-dihydro-6H-purin-6-one 
• 362-76-5 2',3'-isopropylideneguanosine 
• 5391-07-1 9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(methylamino)-1,9-dihydro-6H-purin-6-one 
• 73196-81-3 2',3',5'-tri-O-acetyl-2-N-(p-methylphenylthiomethyl)guanosine 
• 112156-61-3 5-(3-Benzoyl-thioureido)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-imidazole-4-carboxylic acid amide 
• 2627-69-2 AICA riboside 
• 10030-78-1 1,7-dihydro-2-(methylamino)-6H-purin-6-one 
• 107-71-1 tert-butyl peroxyacetate 
• 77312-37-9 2-N-(p-Tolylthiomethyl)-guanosine 
• 4395-48-6 2',3',5'-Tri-O-acetyl-N²-methylguanosine 

Relevant articles and documents

Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations

The RNA-world hypothesis assumes that life on Earth started with small RNA molecules that catalyzed their own formation. Vital to this hypothesis is the need for prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here we show that isocyanates in combination with sodium nitrite establish methylating and carbamoylating reactivity compatible with early Earth conditions. These reactions lead to the formation of methylated and amino acid modified nucleosides that are still extant. Our data provide a plausible scenario for the chemical origin of certain noncanonical bases, which suggests that they are fossils of an early Earth.

METABOLITE BIOMARKERS FOR THE DETECTION OF ESOPHAGEAL CANCER USING MS

Results of studies of nucleosides in biofluid specimens from patients with esophageal adenocarcinoma and related disorders have identified five biomarkers of the conditions: 1-methyladenosine, N2,N2-dimethylguanosine, N2-methylguanosine, cytidine and uridine. In certain embodiments, methods of measuring these biomarkers and kits for measuring these biomarkers are provided.

Conversion of 'AICA-Riboside' into Guanosines

5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide ('AICA-riboside', 2) has been converted into guanosine ; the mechanism of formation of the pyrimidine ring in the nucleoside has been elucidated.