64350-24-9

Usage

Uses

Used in Synthesis of Oligonucleotides:
N2-(2-METHYLPROPANOYL)-GUANOSINE is used as a synthetic building block for the creation of 2''-O-(o-nitrobenzyl)-3''-thioguanosine phosphoramidite. N2-(2-METHYLPROPANOYL)-GUANOSINE is then utilized in the formation of oligonucleotides, which serve as substrates for studying the mechanism of RNA catalysis. The application of N2-(2-METHYLPROPANOYL)-GUANOSINE in this context is crucial for advancing our understanding of RNA's role in various biological processes and its potential as a therapeutic target.
Used in Molecular Biology Research:
In the field of molecular biology, N2-(2-METHYLPROPANOYL)-GUANOSINE is used as a key component in the synthesis of modified nucleotides and oligonucleotides. These modified molecules can be employed in various research applications, such as the investigation of gene expression, regulation, and function. The use of N2-(2-METHYLPROPANOYL)-GUANOSINE in this industry enables scientists to develop novel tools and techniques for studying the complex interactions within biological systems.
Used in Drug Development:
N2-(2-METHYLPROPANOYL)-GUANOSINE may also find application in the pharmaceutical industry, particularly in the development of new drugs targeting RNA-based mechanisms. The unique properties of this synthetic nucleoside analog make it a promising candidate for the design of novel therapeutic agents that can modulate RNA function, potentially leading to the treatment of various diseases and conditions.

InChI:InChI=1/C14H19N5O6/c1-5(2)11(23)17-14-16-10-7(12(24)18-14)15-4-19(10)13-9(22)8(21)6(3-20)25-13/h4-6,8-9,13,20-22H,3H2,1-2H3,(H2,16,17,18,23,24)/t6-,8-,9-,13-/m1/s1

Upstream product

• 97-72-3 2-Methylpropionic anhydride 
• 118-00-3 G 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 53274-35-4 2',3',5'-O-Trisguanosine 
• 139434-70-1 N-isobutyryl-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2′-O-[(methylthio)methyl]guanosine 
• 1314034-34-8 N₂-isobutyryl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methoxymethyl)guanosine 
• 79-30-1 isobutyryl chloride 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 70337-80-3 N²-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)guanosine 
• 124-41-4 sodium methylate 

Downstream Products

• 67607-83-4 N²-Isobutyroyl-5'-O-(4-methoxytrityl)guanosin 
• 89494-39-3 5'-O-(tert-butyldimethylsilyl)-N²-isobutyrylguanosine 
• 104110-06-7 Thiophosphoric acid O-((2R,3S,4R,5R)-3,4-dihydroxy-5-{2-[(Z)-isobutyrylimino]-6-oxo-1,2,3,6-tetrahydro-purin-9-yl}-tetrahydro-furan-2-ylmethyl) ester O',O''-bis-(4-nitro-phenyl) ester 
• 1300713-90-9 5'-O-(dimethoxytrityl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)guanosine 
• 1586816-15-0 5'-O-(dimethoxytrityl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-guanosine 3′-N,N-diisopropyl(cyanoethyl)phosphoramidite 
• 64350-25-0 N²-isobutyryl-2'-O-(o-nitrobenzyl)guanosine 
• 1586816-16-1 5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine 
• 1586816-14-9 5'-O-(dimethoxytrityl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-thioguanosine-3'-S-(cyanoethyl-N,N-diisopropylphosphoramidite) 

Relevant academic research and scientific papers

Preparation method of 5′-O-(4,4'-dimethoxytriphenylmethyl)-N2-isobutyryl guanosine

The present invention discloses a method for preparing 5 '-O- (4,4'-dimethoxytriphenylmethyl)-N2-isobutyryl guanosine, after the preparation of N2-isobutyryloylguanosine with guanosine as the starting material, dmt-Cl was added to participate in the react

Compositions and Methods for Reverse Automated Nucleic Acid Synthesis

Methods for reverse automated nucleic acid synthesis, and 5′-H-phosphonates suitable for use in the same, as well as methods for making 5′-H-phosphonates, are described.

CYCLIC DINUCLEOTIDES AS STING AGONISTS

Disclosed are compounds, compositions and methods for treating of diseases, syndromes, or disorders that are affected by the modulation of STING. Such compounds are represented by Formula (I) as follows: wherein R, R1B, R1C, R2B

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.

Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives

Nucleoside derivatives are largely synthesized and tested to investigate their influence on platelet aggregation. It's well known that P2Y receptors play an important role in the regulation of platelet function and, as consequence, in controlling atherothrombotic events. The research of compounds that antagonize P2Y1 and, in particular, P2Y12 receptors is of great interest in the aim to obtain platelet aggregation inhibitors that are effective in the prevention and treatment of arterial thrombosis. In this study we present the synthesis and in vitro metabolic stability in human blood and rat liver homogenate of a new class of nucleoside derivatives, in particular 5′-phosphonate adenosine, inosine, guanosine and thioadenosine analogues also modified at the ribose moiety. On the basis of the results obtained we can hypothesize compounds 4 and 18 to have in vivo a relatively high stability.

Synthesis of oligoribonucleotides containing 2'-o-methoxymethyl group by the phosphotriester method

An effective procedure for the synthesis of ribonucleotide monomers containing a 2'-methoxymethyl-modifying group was developed. These monomers were used for the synthesis of RNA fragments by the solid-phase phosphotriester method under O-nucleophilic intramolecular catalysis. The properties of 2'-methoxymethyl-containing oligoribonucleotides were examined. Copyright Taylor and Francis Group, LLC.

COMPOUNDS FOR TREATING BACTERIAL INFECTIONS

The present invention relates to a novel class of guanine nucleotide analogs which inhibit RelA and Relseq synthetic activity and which possess anti-bacterial activity. The present invention also relates to pharmaceutical compositions that include such compounds, and to methods of use of such compounds or compositions for combating bacteria and treating bacterial infections.

Design and synthesis of α-carboxy phosphononucleosides

Rhodium catalyzed O-H insertion reactions employing α- diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5′-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

ppGpp analogues inhibit synthetase activity of Rel proteins from Gram-negative and Gram-positive bacteria

A prominent feature of the stringent response is the accumulation of two unusual phosphorylated derivatives of GTP and GDP (pppGpp: 5′-triphosphate-3′-diphosphate, and ppGpp: 5′-3′-bis-diphosphate), collectively called (p)ppGpp, within a few seconds after the onset of amino-acid starvation. The synthesis of these 'alarmone' compounds is catalyzed by RelA homologues. Other features of the stringent response include inhibition of stable RNA synthesis and modulation of transcription, replication, and translation. (p)ppGpp accumulation is important for virulence induction, differentiation and antibiotic resistance. We have synthesized a group of (p)ppGpp analogues and tested them as competitive inhibitors of Rel proteins in vitro. 2′-Deoxyguanosine-3′-5′-di(methylene bisphosphonate) [compound (10)] was found as an inhibitor that reduces ppGpp formation in both Gram-negative and Gram-positive bacteria. In silico docking together with competitive inhibition analysis suggests that compound (10) inhibits activity of Rel proteins by competing with GTP/GDP for its binding site. As Rel proteins are completely absent in mammalians, this appears to be a very attractive approach for the development of novel antibacterial agents.

Synthesis of guanosine 5′-conjugates and their use as initiator molecules for transcription priming

We have synthesised two guanosine derivatives that are linked to biotinylated adenosine moieties by using two different strategies, one that includes synthetic steps on the solid phase and another one that is performed entirely in solution. The synthesised derivatives were shown to function as initiator molecules in transcription priming experiments. The incorporation efficiency was determined to be approximately 2%. Even though this value is rather low, the use of either molecule in selection experiments seems reasonable. Basically, RNA libraries with sequence complexities of 10 15 to 1016 can be generated. Labelling of such a library with our initiator molecule would still produce 1013 to 10 14 labelled/functionalised sequences, and thus sufficient sequence space for selection. The Royal Society of Chemistry.