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

Definition

ChEBI: Guanosine with the hydrogen on the amine at position N-2 substituted with a methyl group.

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

• 4395-48-6 2',3',5'-Tri-O-acetyl-N²-methylguanosine 
• 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 
• 130469-17-9 2',3',5'-Tri-O-acetyl-N²-(1,3-benzodithiol-2-yl)guanosine 
• 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 
• 58917-66-1 2',1''-anhydro-5-<(1''-benzamido-1''-hydroxymethylene)amino>-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 74-89-5 methylamine 
• 107-71-1 tert-butyl peroxyacetate 

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.

Production, characterization and synthetic application of a purine nucleoside phosphorylase from Aeromonas hydrophila

Purine nucleoside phosphorylase (PNP) from Aeromonas hydrophila encoded by the deoD gene has been over-expressed in Escherichia coli, purified, characterized about its substrate specificity and used for the preparative synthesis of some 6-substituted purine-9-ribosides. Substrate specificity towards natural nucleosides showed that this PNP catalyzes the phosphorolysis of both 6-oxo- and 6-aminopurine (deoxy)ribonucleosides. A library of nucleoside analogues was synthesized and then submitted to enzymatic phosphorolysis as well. This assay revealed that 1-, 2-, 6- and 7-modified nucleosides are accepted as substrates, whereas 8-substituted nucleosides are not. A few transglycosylation reactions were carried out using 7-methylguanosine iodide (4) as a d-ribose donor and 6-substituted purines as acceptor. In particular, following this approach, 2- amino-6-chloropurine-9-riboside (2c), 6-methoxypurine- 9-riboside (2d) and 2-amino-6-(methylthio)purine- 9-riboside (2g) were synthesized in very high yield and purity.

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.