2140-65-0

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 
• 58917-66-1 2',1''-anhydro-5-<(1''-benzamido-1''-hydroxymethylene)amino>-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 74-89-5 methylamine 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 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 
• 485-80-3 S-adenosyl-L-methionine 
• 684-93-5 1-methyl-1-nitrosourea 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 126832-41-5 5'-O-dimethoxytrityl-N₁-methyl-2'-O-(tetrahydropyran-2-yl)guanosine 
• 27964-07-4 1-methyl-8-hydroxyguanosine 
• 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 
• 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 academic research and scientific papers

Tautomers of one-electron-oxidized guanosine

(Chemical Equation Presented) Aminic or iminic: Two tautomeric forms of oxidized guanosine have been produced by chemical radiation methods - by direct oxidation of guanosine or from the protonation of the 8-bromoguanosine electron adduct - and identified. The tautomerization from the iminic to the aminic arrangement has an activation energy of 23.0 kJ mol-1 and occurs through a complex transition state (see scheme).

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.

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

For investigating the stability of C(8)-fluorine bond in 8-fluoropurine nucleosides some protected 8-fluoroguanosine, 8-fluoroinosine and 8-fluoroadenosine derivatives were prepared by direct fluorination of acetyl-protected purine nucleosides with elemental fluorine in solvents such as chloroform, acetonitrile and nitromethane. Fluorination reactions conducted in chloroform medium gave better yields of 8-fluoropurines. The fluorination yields were slightly lower when acetonitrile or nitromethane was used as solvent, but the product purification was found to be much easier. When the synthesized, protected fluoronucleosides were subjected to standard basic (NH3 in methanol or 2-propanol) and acidic (HCl in methanol) deprotection conditions relevant to nucleoside chemistry, an efficient defluorination reaction took place. The kinetics of these defluorination reactions were conveniently followed, under pseudo-first-order reaction conditions, using 19F NMR spectroscopy. 1H NMR, LC-MS and mass spectroscopy identified the products of the kinetic reaction mixtures. The defluorination reaction rate constants (kobs) in basic media depended upon the electron density at C(8) while the kobs data in acidic medium were determined by the pKa of N7. An addition-elimination based mechanism (SNAr) has been proposed for the defluorination reactions of these 8-fluoropurine nucleosides.

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.

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.

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.

The Synthesis of 2′-O-[(Triisopropylsilyl)oxy] methyl (TOM) Phosphoramidites of Methylated Ribonucleosides (m1G, m2G, m22G, m1I, m3U, m4C, m6A, m62A) for Use in Automated RNA Solid-Phase Synthesis

The straightforward synthesis of eight methylated ribonucleoside phosphoramidites is described. These building blocks allow for incorporation of the naturally occuring nucleosides 1-methylguanosine (m1G), N 2-methylguanosine (m2G), N2N 2-dimethylguanosine (m22G), 1-methylinosine (m1I), 3-methyluridine (m3U), N4- methylcytidine (m4C), N6-methyladenosine (m6A), and N6,N6-dimethyladenosine (m62A) into oligoribonucleotides by automated RNA solid-phase synthesis. In all cases, the ribose 2′-hydroxyl group of the building blocks is masked by the recently introduced [(triisopropylsilyl)oxy]methyl (TOM) group.

Reaction of arylnitrenium ions with guanine derivatives: N1-methylguanosine and N2,N2-dimethylguanosine

A prior flash photolysis study of the direct reaction of arylnitrenium ions with 2′-deoxyguanosine identified a second intermediate that grew in as the transient nitrenium ion reacted with the nucleoside. This intermediate was identified as the the product of the addition of the nitrenium ion to the C-8 position of guanine prior to loss of the C-8 proton - the C-8 intermediate. A feature of the C-8 intermediate is that it exists in acid-base forms. This behavior was evident in both a spectroscopic analysis as well as in the rate-pH profile, which showed a break around pH 4 from a pH-independent reaction to a reaction that was first-order in H+. The present study was designed to identify the structure of the conjugate base form. This involved a kinetic study of the decay of the C-8 intermediate derived from the reaction of the 2-fluorenylnitrenium ion with N1-methylguanosine and N2,N2-dimethylguanosine. The rationale was that the former is unable to lose the N-1 proton, while the latter cannot deprotonate at the NH2 group. The rate-pH profiles clearly show that it is the N-1 proton that is acidic. The rate constants for the C-8 intermediate of N2,N2-dimethylguanosine show the same downward break observed with 2′-deoxyguanosine and guanosine associated with conversion to the conjugate base form. In contrast, the rate constants for the N1-methylguanosine intermediate are independent of pH. Rate constants for the reaction forming the C-8 intermediate are also reported. These show that the reaction of nitrenium ions with the N2,N2-dimethylguanine derivative is significantly faster (except where the reactions are diffusion controlled). This is consistent with the initial step of the reaction of an arylnitrenium ion and guanine occurring by direct addition at C-8. The developing positive charge in such a reaction can be delocalized to the C-2 position where π donors such as NH2 and NMe2 can exert a stabilizing effect.

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.