69992-10-5

Basic information

• Product Name: 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE
• Synonyms: 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE;3',5'-DI-O-ACETYL-2'-DEOXYGUANOSINE;3',5'-Di-O-acetyl-2'-deoxy-D-guanosine;Nsc76761;2'-Deoxy-guanosine 3',5'-Diacetate;2'-Deoxyguanosine 3',5'-Diacetate;3',5'-Di-O-acetyldeoxyguanosine;3',5'-O-Diacetyl-2'-deoxyguanosine
• CAS NO: 69992-10-5
• Molecular Formula: C₁₄H₁₇N₅O₆
• Molecular Weight: 351.31
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 69992-10-5.mol

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 625.5°C at 760 mmHg
• Flash Point: 332.1°C
• Appearance: /
• Density: 1.72g/cm³
• Vapor Pressure: 1.46E-15mmHg at 25°C
• Refractive Index: 1.724
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE(69992-10-5)
• EPA Substance Registry System: 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE(69992-10-5)

Safety Data

• Hazardous Substances Data: 69992-10-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2'-Deoxy-3',5'-di-O-acetylguanosine is used as a key intermediate in the synthesis of various nucleoside analogs and modified nucleotides. Its unique chemical structure allows for the development of novel compounds with potential applications in different fields, such as pharmaceuticals and biotechnology.
Used in Antiviral Research:
In the field of antiviral research, 2'-Deoxy-3',5'-di-O-acetylguanosine is employed as a starting material for the development of new antiviral agents. Its reactivity with hypobromous acid (HOBr) can be exploited to create modified nucleosides that may exhibit antiviral properties, potentially leading to the discovery of new treatments for viral infections.
Used in Biochemical Studies:
2'-Deoxy-3',5'-di-O-acetylguanosine is also utilized in biochemical studies to investigate the interactions between nucleosides and various enzymes or proteins. Understanding these interactions can provide valuable insights into the mechanisms of nucleic acid metabolism and the development of new therapeutic strategies.
Used in Analytical Chemistry:
As a white powder with distinct chemical properties, 2'-Deoxy-3',5'-di-O-acetylguanosine can be used as a reference compound in analytical chemistry. It can help in the development and validation of analytical methods for the detection and quantification of nucleosides and their derivatives in various samples, such as biological fluids and pharmaceutical formulations.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2'-Deoxy-3',5'-di-O-acetylguanosine is used as a building block for the synthesis of innovative drug candidates. Its unique structure and reactivity make it a valuable component in the development of new drugs with potential applications in various therapeutic areas, including oncology, virology, and cardiovascular diseases.
Used in Biotechnology:
2'-Deoxy-3',5'-di-O-acetylguanosine also finds applications in the biotechnology sector, where it can be employed in the design and synthesis of novel bioactive molecules. These molecules may have potential applications in gene therapy, molecular diagnostics, and the development of new tools for genetic engineering and synthetic biology.

InChI:InChI=1/C14H17N5O6/c1-6(20)23-4-9-8(24-7(2)21)3-10(25-9)19-5-16-11-12(19)17-14(15)18-13(11)22/h5,8-10H,3-4H2,1-2H3,(H3,15,17,18,22)

Upstream product

• 108-24-7 acetic anhydride 
• 961-07-9 2'-Deoxyguanosine 
• 763103-11-3 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[2-amino-6-(2-trimethylsilanyl-ethoxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 763103-12-4 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(2-trimethylsilanyl-ethoxy)-2-(2-trimethylsilanyl-ethoxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 961-07-9 2'-deoxyguanosine 
• 92447-23-9 6-O-(3,5-dichlorophenyl)-2-N-phenylacetyl-2'-deoxyguanosine 

Downstream Products

• 105821-12-3 3',5'-di-O-acetyl-2'-deoxy-2-N-(di-p-methoxytrityl)guanosine 
• 705255-07-8 3',5'-di-O-acetyl-2'-deoxy-2-N-(mono-p-methoxytrityl)guanosine 
• 763103-13-5 [9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2-trimethylsilanyl-ethoxy)-9H-purin-2-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 83061-20-5 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(dimethylamino)purine 
• 964-21-6 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine 
• 111244-92-9 2'-deoxy-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 148144-80-3 2'-deoxy-5'-O-(monomethoxytrityl)-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 
• 131920-31-5 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 259675-33-7 2'-deoxy-O⁶-methyl-N²-[2-(4-nitrophenyl)ethoxycarbonyl]guanosine 
• 259675-32-6 3',5'-di-O-acetyl-2'-deoxy-O⁶-methyl-N²-[2-(4-nitrophenyl)ethoxycarbonyl]guanosine 
• 259675-36-0 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-O⁶-methyl-N²-[2-(4-nitrophenyl)ethoxycarbonyl]guanosine 
• 132183-39-2 2-fluoro-O⁶-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine 
• 86137-72-6 2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 
• 153527-28-7 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2'-deoxy-2-fluoroinosine 

Relevant articles and documents

Discovery and mutagenicity of a guanidinoformimine lesion as a new intermediate of the oxidative deoxyguanosine degradation pathway

Oxidative degradation of DNA is a major mutagenic process. Reactive oxygen species (ROS) produced in the course of oxidative phosphorylation or by exogenous factors are known to attack preferentially deoxyguanosine. The latter decomposes to give mutagenic lesions, which under physiological conditions are efficiently repaired by specialized maintenance systems in the cell. Although many intermediates of the degradation pathway are today well-known, we report in this study the discovery of a new intermediate with an interesting guanidinoformimine structure. The structure elucidation of the new lesion was possible by using HPLC-MS techniques and organic synthesis. Finally we report the mutagenic potential of the new lesion in comparison to the known lesions imidazolone and oxazolone using primer extension and pyrosequencing experiments.

PHOSPHATE AND PHOSPHONATE BASED COMPOUNDS OF 6-THIO-2'-DEOXYGUANOSINE AS ANTI-CANCER AGENTS

Phosphates and phosphonates compounds of 6-thio-2'-deoxyguanosine are provided. The uses and pharmaceutical compositions of these compounds are disclosed.

NUCLEOTIDE PRODRUGS

The invention relates to nucleotide prodrugs and pharmaceutical preparations thereof. The invention further relates using the prodrugs of the invention in the treatment of mitochondrial DNA (mtDNA) depletion syndrome (MDS).

6-disulfide-substituted-2'-deoxyguanosine compound and preparation method and application thereof

The invention provides a 6-disulfide-substituted-2'-deoxyguanosine compound and a preparation method thereof and an application thereof in an anti-tumor drug. The preparation method is capable of using 2'-deoxyguanosine as a structure mother nucleus, designing and synthesizing a series of brand-new thioredoxin-1(Trx-1) inhibitors. The compound is a structure as shown in a formula I, and Trx-1 activity inhibition testing is performed on the type of the compounds, apparent inhibitory activity is shown. It is indicated from in vitro and vivo research that these compounds show the remarkable tumorinhibitory effect to multiple types of tumor, can be applied to the drugs of the tumor related to human body cell proliferation, and provide a new way for the research of the anti-cancer drugs.

Modified Nucleotides for Discrimination between Cytosine and the Epigenetic Marker 5-Methylcytosine

5-Methyl-2′-deoxycytosine, the most common epigenetic marker of DNA in eukaryotic cells, plays a key role in gene regulation and affects various cellular processes such as development and carcinogenesis. Therefore, the detection of 5mC can serve as an important biomarker for diagnostics. Here we describe that modified dGTP analogues as well as modified primers are able to sense the presence or absence of a single methylation of C, even though this modification does not interfere directly with Watson-Crick nucleobase pairing. By screening several modified nucleotide scaffolds, O6-modified 2′-deoxyguanosine analogues were identified as discriminating between C and 5mC. These modified nucleotides might find application in site-specific 5mC detection, for example, through real-time PCR approaches.

Synthesis of oligonucleotides carrying fluorescently labelled O6-alkylguanine for measuring hAGT activity

O6-alkylguanine-DNA-alkyltransferase (hAGT) activity provides resistance to cancer chemotherapeutic agents and its inhibition enhances chemotherapy. We herein present the development of a novel fluorescence assay for the detection of hAGT activity. We designed a dsDNA sequence containing a fluorophore-quencher pair, where the fluorophore was attached to an O6-benzylguanine. This precursor was synthesized using the Mitsunobu reaction to introduce the benzyl group. The alkyl-fluorophore group is transferred to the active site during the dealkylation, producing an increase in fluorescence which is correlated to hAGT activity. This assay can be used for the evaluation of potential inhibitors of hAGT in a straightforward manner.

Chain-terminating and clickable NAD+ analogues for labeling the target proteins of ADP-ribosyltransferases

ADP-ribosyltransferases (ARTs) use NAD+ as a substrate and play important roles in numerous biological processes, such as the DNA damage response and cell cycle regulation, by transferring multiple ADP-ribose units onto target proteins to form poly(ADP-ribose) (PAR) chains of variable sizes. Efforts to identify direct targets of PARylation, as well as the specific ADP-ribose acceptor sites, must all tackle the complexity of PAR. Herein, we report new NAD+ analogues that are efficiently processed by wild-type ARTs and lead to chain termination owing to a lack of the required hydroxy group, thereby significantly reducing the complexity of the protein modification. Due to the presence of an alkyne group, these NAD+ analogues allow subsequent manipulations by click chemistry for labeling with dyes or affinity markers. This study provides insight into the substrate scope of ARTs and might pave the way for the further developments of chemical tools for investigating PAR metabolism.

Trifluoromethyl derivatives of canonical nucleosides: Synthesis and bioactivity studies

The use of the system CF3SO2Na/tert-butyl- hydroperoxide (tert-ButOOH), recently reported for the efficient trifluoromethylation of a variety of heterocyclic aromatic compounds, has been here profitably exploited for the synthesis of 5-CF3-2′- deoxycytidine, 8-CF3-2′-deoxyadenosine, 8-CF 3-2′-deoxyguanosine and 8-CF3-inosine, regioselectively obtained in good to acceptable yields following a very simple protocol. The bioactivity of these modified nucleosides, and particularly of the novel 8-CF3-2′-deoxyguanosine and 8-CF3-inosine, has been evaluated on a panel of tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays.

Stabilization of DNA duplex by 2-substituted adenine as a minor groove modifier

2-(1-Naphthalenylethynyl)-2′-deoxyadenosine (NA) was synthesized and incorporated into oligodeoxynucleotides. DNA duplexes containing newly designed 5′-NAT-3′/3′-TNA- 5′ base pairs are considerably stabilized than unmodifi

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.