2140-65-0

Basic information

• Product Name: 1-METHYLGUANOSINE
• Synonyms: 1-METHYLGUANOSINE;2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1-methyl-1,9-dihydropurin-6-one;1-Methyl-2-amino-9-(β-D-ribofuranosyl)-9H-purine-6(1H)-one;1-Methyl-2-amino-9-β-D-ribofuranosyl-9H-purine-6(1H)-one;Guanosine, 1-methyl- (8ci)(9ci);N1-Methylguanosine;Nsc 70897;RNA-modified nucleoside m1G
• CAS NO: 2140-65-0
• Molecular Formula: C₁₁H₁₅N₅O₅
• Molecular Weight: 297.27
• Mol File: 2140-65-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 163 °C
• Boiling Point: 737.4°Cat760mmHg
• Flash Point: 399.7°C
• Appearance: /
• Density: 2.02g/cm³
• Vapor Pressure: 7.91E-23mmHg at 25°C
• Refractive Index: 1.86
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 13.22±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1-METHYLGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLGUANOSINE(2140-65-0)
• EPA Substance Registry System: 1-METHYLGUANOSINE(2140-65-0)

Safety Data

• Hazardous Substances Data: 2140-65-0(Hazardous Substances Data)

Usage

Definition

ChEBI: Guanosine substituted with a methyl group at position N-1.

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

Upstream product

• 512-56-1 trimethyl phosphite 
• 118-00-3 G 
• 17287-03-5 trimethylsulphonium hydroxide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 353-39-9 Trimethylsulfonium Fluoride 
• 76462-74-3 n-Butyldimethylsulfonium Fluoride 
• 2627-69-2 AICA riboside 
• 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 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 18412-81-2 dodecyl-dimethylsulphonium iodide 
• 118-00-3 guanosine 
• 684-93-5 1-methyl-1-nitrosourea 
• 485-80-3 S-adenosyl-L-methionine 

Downstream Products

• 611-59-6 paraxanthine 
• 26758-00-9 1,7-dimethylguanine 
• 1431944-93-2 7-N-p-methoxybenzyl-1-methylguanine 
• 938-85-2 1-methylguanine 
• 1404304-99-9 N²,3-etheno-2'-isopropyl-1-methylguanine 
• 1431944-99-8 C₁₉H₂₁N₅O₅S 
• 1431944-96-5 C₁₉H₂₄N₅O₃⁽¹⁺⁾*Br^(1-) 
• 1431944-95-4 7-N-(p-methoxybenzyl)acremolin 
• 1431944-94-3 9-N-p-methoxybenzyl-1-methylguanine 
• 27964-07-4 1-methyl-8-hydroxyguanosine 
• 126832-41-5 5'-O-dimethoxytrityl-N₁-methyl-2'-O-(tetrahydropyran-2-yl)guanosine 
• 661471-73-4 N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-1-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]guanosine 
• 661471-72-3 N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-1-methylguanosine 

Relevant articles and documents

A convenient method for the synthesis of N2,N2-dimethylguanosine by reductive C-S bond cleavage with tributyltin hydride

-

Pyruvate is the source of the two carbons that are required for formation of the imidazoline ring of 4-demethylwyosine

TYW1 catalyzes the condensation of N-methylguanosine with two carbon atoms from an unknown second substrate to form 4-demethylwyosine, which is a common intermediate in the biosynthesis of all of the hypermodified RNA bases related to wybutosine found in eukaryal and archaeal tRNAPhe. Of the potential substrates examined, only incubation with pyruvate resulted in formation of 4-demethylwyosine. Moreover, incubation with C1, C2, C3, or C1,2,3-13C-labeled pyruvate showed that C2 and C3 are incorporated while C1 is not. The mechanistic implications of these results are discussed in the context of the structure of TYW1.

Preparation method of paraxanthine

The invention discloses a preparation method of paraxanthine, which comprises the following steps: carrying out N methylation on 7-site and 1-site of guanine nucleoside (V), hydrolyzing glycosyl to obtain a compound (II), reacting the compound (II) with a diazotization reagent, and hydrolyzing to obtain the paraxanthine (I). The raw materials and the auxiliary materials are cheap and easy to obtain, and the industrial price of the main raw material guanosine is only 90 yuan/KG; the steps are short, and the total yield is not less than 70%; the reaction conditions are mild, and the method is safe and reliable; and the method is simple to operate, stable in process and suitable for industrialization.

Acremolin from acremonium strictum is N 2,3-etheno-2′- isopropyl-1-methylguanine, not a 1 H -azirine. Synthesis and structural revision

The first synthesis of the heterocyclic marine natural product, acremolin, is reported along with the revision of the structure from a 1H-azirine to a substituted N2,3-ethenoguanine (5-methyl-7-isopropyl-4,5- dihydroimidazo[2,1-b]purine). Additional properties of acremolin are also described including its 1H-15N-HMBC and fluorescence spectra.