7803-88-5

Basic information

• Product Name: O6-METHYLGUANOSINE
• Synonyms: O6-METHYLGUANOSINE;o-methoxydeoxyguanosine;o-methyl-guanosin;6-O-METHYLGUANOSINE;2-Amino-6-methoxy-9-b-D-ribofuranosyl-9H-purine;2-Amino-6-methoxypurine Ribonucleoside;6-Methoxy-9-b-D-ribofuranosyl-9H-purin-2-amine;NSC 66381
• CAS NO: 7803-88-5
• Molecular Formula: C₁₁H₁₅N₅O₅
• Molecular Weight: 297.27
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides
• Mol File: 7803-88-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 120 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• Boiling Point: 721 °C at 760 mmHg
• Flash Point: 389.9 °C
• Appearance: /
• Density: 1.98 g/cm³
• Vapor Pressure: 8.06E-22mmHg at 25°C
• Refractive Index: 1.829
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Very Slightly), Water (Slightly)
• PKA: 13.07±0.70(Predicted)
• CAS DataBase Reference: O6-METHYLGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: O6-METHYLGUANOSINE(7803-88-5)
• EPA Substance Registry System: O6-METHYLGUANOSINE(7803-88-5)

Safety Data

• Hazardous Substances Data: 7803-88-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 7803-88-5 differently. You can refer to the following data:
1. A guanine derivative that acts as modulators of GTPases and modulator-resistant enzymes; used in drug design and target validation.
2. 6-O-Methyl Guanosine is a guanine derivative that acts as modulators of GTPases and modulator-resistant enzymes; used in drug design and target validation

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

Upstream product

• 58-63-9 Inosine 
• 20535-83-5 O-methylguanine 
• 67-56-1 methanol 
• 3387-63-1 2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 118-00-3 G 
• 17287-03-5 trimethylsulphonium hydroxide 

Downstream Products

• 116137-82-7 O⁶,7-dimethylguanine 
• 132121-67-6 2-Acetonyl-9-(3'-deoxy-β-D-ribofuranosyl)hypoxanthine 
• 153248-58-9 (2R,3R,4R,5R)-5-(2-acetamido-6-methoxy-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl but-3-yn-1-yl diisopropylphosphoramidite 

Relevant articles and documents

Flow-Synthesis of Nucleosides Catalyzed by an Immobilized Purine Nucleoside Phosphorylase from Aeromonas hydrophila: Integrated Systems of Reaction Control and Product Purification

A purine nucleoside phosphorylase from Aeromonas hydrophyla (AhPNP) was covalently immobilized in a pre-packed stainless steel column containing aminopropylsilica particles via Schiff base chemistry upon glutaraldehyde activation. The resulting AhPNP-IMER (Immobilized Enzyme Reactor, immobilization yield ≈50%) was coupled on-line through a 6-way switching valve to an HPLC apparatus containing an analytical or a semi-preparative chromatographic column. The synthesis of five 6-modified purine ribonucleosides was carried out by continuously pumping the reaction mixture through the AhPNP-IMER until the highest conversion was reached, and then directing the reaction mixture to chromatographic separation. The conditions of the AhPNP-catalyzed transglycosylations (2:1 ratio sugar donor:base acceptor; 10 mM phosphate buffer; pH 7.5; temperature 37 °C, flow rate 0.5 mL min-1) were optimized by a fractional factorial experimental design. Coupling the bioconversion step with the product purification in such an integrated platform resulted in a fast and efficient synthetic process (yield=52-89%; 10 mg) where sample handling was minimized. To date, AhPNP-IMER has retained completely its activity upon 50 reactions in 10 months.

SELECTIVE METHYLATION OF NUCLEOSIDES

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Methylation of Nucleosides with Trimethylsulfonium Hydroxide. Effects of Transition Metal Ions

The effect of transition metal acetylacetonates on the methylation of ribo- and deoxyribonucleosides with trimethylsulfonium hydroxide was studied.With ribonucleosides the metal complexes promoted O'-methylation at the 2' and 3' positions of the ribosyl group.A comparable effect was not observed in methylation of deoxyribonucleosides.These results are attributed to an increase in the nucleophilicity of the 2'-OH and 3'-OH groups of the ribosides through complex formation with the metal ion; such a complex cannot form with the deoxyribose derivatives.The activity of the metal ions studied for promoting this O'-methylation increased in the order Mn2+ 2+ = Zn2+ 2+ 2+ 3+.These M(AA)n also suppressed N-methylation of the purine and pyrimidine rings of adenosine and cytidine.It is suggested that this result may be caused by coordination of the metal ions with ring nitrogens.