3676-72-0

Usage

Uses

Used in Pharmaceutical Industry:
N2-Benzoyl-D-guanosine is used as a building block for the synthesis of oligoribonucleotides, which are short sequences of ribonucleic acids (RNA). These oligoribonucleotides have various applications in the pharmaceutical industry, including the development of antisense drugs, RNA interference (RNAi) therapies, and the creation of artificial ribonucleic acid molecules for research purposes.
Used in Research and Development:
In the field of research and development, N2-Benzoyl-D-guanosine is utilized for the synthesis of modified RNA molecules with specific properties. These modified RNA molecules can be used to study the structure, function, and interactions of RNA in biological systems, contributing to a better understanding of RNA biology and its role in various diseases.
Used in Diagnostics:
N2-Benzoyl-D-guanosine can also be employed in the development of diagnostic tools and assays that rely on the detection or manipulation of RNA molecules. These diagnostic applications can help in the early detection of diseases, monitoring of treatment responses, and the study of disease progression.
Overall, N2-Benzoyl-D-guanosine plays a significant role in various applications across the pharmaceutical, research, and diagnostic industries due to its importance in the synthesis of oligoribonucleotides and modified RNA molecules.

InChI:InChI=1/C17H17N5O6/c23-6-9-11(24)12(25)16(28-9)22-7-18-10-13(22)19-17(21-15(10)27)20-14(26)8-4-2-1-3-5-8/h1-5,7,9,11-12,16,23-25H,6H2,(H2,19,20,21,26,27)/t9-,11-,12-,16-/m1/s1

Upstream product

• 80015-56-1 2'-O-(4-methoxybenzyl)-N²-benzoylguanosine 
• 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 
• 98-88-4 benzoyl chloride 
• 532-55-8 Benzoyl isothiocyanate 
• 118-00-3 G 
• 53274-35-4 2',3',5'-O-Trisguanosine 
• 28288-50-8 N²,O^2',O^3',O^5'-tetrabenzoylguanosine 

Downstream Products

• 71171-58-9 N²-benzyl-2'-deoxyguanosine 
• 81794-15-2 N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide 
• 81794-14-1 N-{9-[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide 
• 87985-92-0 2'-O-(4-methoxybenzyl)-3',5'-di-O-acetyl-N²-benzoylguanosine 
• 87985-93-1 N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide 
• 88015-19-4 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester 
• 87985-94-2 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester 
• 87125-07-3 2-N-benzoyl-2'-O-tetrahydropyranyl-5'-O-dimethoxytritylguanosine-3'-(p-chlorophenyl-2-cyanoethyl)phosphate 
• 87125-14-2 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 
• 97626-10-3 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 2-cyano-ethyl ester 
• 72409-45-1 N²-Benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)guanosin 
• 72409-43-9 N²-Benzoyl-2'-O-(tert-butyldimethylsilyl)guanosin 
• 72409-44-0 N²-Benzoyl-3'-O-(tert-butyldimethylsilyl)guanosin 

Relevant academic research and scientific papers

New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors

Design and development of nucleoside analogs is an established strategy in the antiviral drug discovery field. Nevertheless, for many viruses the coverage of structure-activity relationships (SAR) in the nucleoside chemical space is not sufficient. Here we present the nucleoside SAR exploration for tick-borne encephalitis virus (TBEV), a member of Flavivirus genus. Promising antiviral activity may be achieved by introduction of large hydrophobic substituents in the position 6 of adenosine or bulky silyl groups to the position 5′. Introduction of methyls to the ribose moiety does not lead to inhibition of TBEV reproduction. Possible mechanisms of action of these nucleosides include the inhibition of viral entry or interaction with TBEV non-structural protein 5 methyltransferase or RNA-dependent RNA polymerase domains.

An improved transient method for the synthesis of N-benzoylated nucleosides

The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCl) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

Synthesis of Guanosines and Deoxyguanosines from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide ('AICA-riboside')

Methods are described for the synthesis of 15N-labelled guanosines and deoxyguanosines, suitable for incorporation into oligonucleotides.The 15N is located at N-1 (e.g. guanosine 1a and deoxyguanosine 1b> or at the NH2 (e.g. guanosine 1

Modification of the amino group of guanosine by methylglyoxal and other α-ketoaldehydes in the presence of hydrogen peroxide

Methylglyoxal is directly mutagenic to Salmonella typhimurium TA100 and its mutagenicity is markedly enhanced in the presence of hydrogen peroxide. We found that methylglyoxal in phosphate buffer was decomposed easily by hydrogen peroxide at room temperature to yield acetic acid and formic acid as major products and diacetyl as a minor product; acetyl radical was detected in the solution by ESR spectroscopy by the use of a spin-trapping reagent, 5,5-dimethyl-1-pyrroline N-oxide. Furthermore, guanosine was converted into N2-acetylguanosine by a combination of methylglyoxal and hydrogen peroxide in 0.1 M phosphate buffers (pH 6.1 to 7.4). This acetylation may be related to the enhancement of methylglyoxal mutagenicity by hydrogen peroxide. Other α-ketoaldehydes such as glyoxal and phenylglyoxal also yielded the corresponding acids and α-dicarbonyls upon reaction with hydrogen peroxide under the same conditions as above. These acids would have been produced through Baeyer-Villiger reaction or coupling of acyl radical with hydroxy radical, and dicarbonyls by dimerization of acyl radicals. In addition, when phenylglyoxal was used, the generation of benzoyl radical and the conversion of guanosine to N2-benzoylguanosine were observed. However, it remains to be established whether the generation of acyl radicals is directly involved in the N-2 acylation of guanosine.

An Improved Method for the Application of the 4-Methoxybenzyl Group to Protect the 2'-Hydroxyl Group in the Ribonucleotide Synthesis by TFA-acidolysis

The cleavage of the 4-methoxybenzyl group from the 2'-OH-position of ribonucleosides by the hydrogenation with different Pd-catalysts as well as trifluoroacetic acid has been studied in detail.During hydrogenation, side reactions at the base residue of cytidine occurred which, however, could be extensively suppressed by PdCl2 catalysis.More practicable results were obtained with trifluoroacetic acid in the presence of cation scavengers, allowing smoothly to convert a series of 2'-methoxybenzyl ribonucleotides to the homogeneous deprotection products.

Application of the Tetraisopropyldisiloxane-1,3-diyl Group in the Chemical Synthesis of Oligoribonucleotides

The application of the tetraisopropyldisiloxane-1,3-diyl (TIPDSi) group for the large-scale preparation of the key components for the chemical synthesis of oligoribonucleotides by the triester approach is described. The key components, N-benzol-2'-O-tetra

Synthesis of Ribooligonucleotides Using the 4-Methoxybenzyl Group as a New Protecting Group for the 2'-Hydroxyl Group

The 4-methoxybenzyl group was introduced to protect the 2'-hydroxyl group of uridine, cytidine, and N2-benzoylguanosine by treatment of 2',3'-O-(dibutylstannylene)uridine or NaH-treated nucleosides with 4-methoxybenzyl bromide.The 2'-O-(4-methoxybenzyl)nucleosides can be used as useful starting materials for the synthesis of 3',5'-linked ribooligonucleotides.The 4-methoxybenzyl group was removed rapidly from the ribooligonucleotides by treatment with triphenylmethyl fluoroborate, and the completely deblocked ribooligonucleotides were characterized by enzymatic hydrolysis.