19962-37-9

Usage

Chemical Properties

White Crystalline

Uses

Protected guanine

InChI:InChI=1/C7H7N5O2/c1-3(13)10-7-11-5-4(6(14)12-7)8-2-9-5/h2H,1H3,(H3,8,9,10,11,12,13,14)

Upstream product

• 108-24-7 acetic anhydride 
• 73-40-5 guanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 51093-31-3 2,6-diamino-5-formylamino-4-hydroxypyrimidine 
• 73-40-5 2-amino-6-hydroxypurine 
• 112233-74-6 N₂-acetyl-O₆-(diphenylcarbamoyl)guanine 
• 917239-36-2 9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-guanine 
• 3056-33-5 2,9-diacetylguanine 
• 917239-35-1 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine 
• 917239-37-3 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-guanine 

Downstream Products

• 1173826-18-0 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-3'-ethoxycarbonylmethyl-2-N-acetylguanosine 
• 4318-06-3 N²-acetyldeoxyguanosine 
• 208175-46-6 2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-guanosine 
• 208758-60-5 N-{7-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-ethoxymethyl]-6-oxo-6,7-dihydro-1H-purin-2-yl}-acetamide 
• 229469-53-8 (1R,3S,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-7-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane 
• 229469-42-5 (1R,3S,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-9-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane 
• 229469-54-9 (1R,3R,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-9-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane 
• 75128-73-3 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one 
• 406215-16-5 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-yl)-N-benzyl-N-[2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-ethyl]-acetamide 
• 406215-17-6 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-N-benzyl-N-[2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-ethyl]-acetamide 

Relevant academic research and scientific papers

Voltammetric study of the affinity of divalent heavy metals for guanine-functionalized iron oxide nanoparticles

In this study, a novel nanobiomaterial based on (3-aminopropyl)triethoxysilane (APTES)-coated iron oxide (Fe3O4) nanoparticles functionalized with newly synthesized guanine hydrazide (GH) was elaborated. A boron-doped diamond electrode coated with GH-APTES–Fe3O4 nanoparticles was used to assess the interaction of heavy metal ions with guanine hydrazide. The adsorption isotherms were electrochemically investigated and it was shown that the adsorption capacity of the nanoparticles towards heavy metals decreased in the following order: Cu2+ > Pb2+ > Cd2+. From the calibration curves, the sensitivities of detection were as follows: 171.6 μA/μM for Cu(II), 156 μA/μM for Pb(II), and 101.4 μA/μM for Cd(II). Graphic abstract: [Figure not available: see fulltext.].

Small Molecules in the Cone Snail Arsenal

Cone snails are renowned for producing peptide-based venom, containing conopeptides and conotoxins, to capture their prey. A novel small-molecule guanine derivative with unprecedented features, genuanine, was isolated from the venom of two cone snail species. Genuanine causes paralysis in mice, indicating that small molecules and not just polypeptides may contribute to the activity of cone snail venom.

Synthetic method 2 -amino -6 - chloropurine

The invention provides a synthetic method of 2 - amino -6 - chloropurine, and belongs to the field of organic synthesis. The synthesis method provided by the invention comprises the following steps: adding 2 -acetyl-6-hydroxypurine into the reaction container. The product and comprises hexachloroacetone, organic base A chloride, heating reflux reaction 2h - 48h, distillation to remove dimethyl sulfoxide, adding alkali liquor pH, reacting 1h - 12h, adjusting 7.0 - 7.5 to 2 - and separating and purifying to obtain the amino -6 - chloropurine of the target product. The nitrogen-containing phosphorus-containing reagent is greatly reduced, the emission of nitrogen-containing phosphorus-containing wastewater is reduced correspondingly, and large-scale process production is facilitated.

Preparation method of acyclovir intermediate N(2),9-diacetyl guanine

The invention discloses a preparation method of an acyclovir intermediate N(2),9-diacetyl guanine, which comprises the following steps: dissolving 2, 4-diamino-6-hydroxy-5-formamido pyrimidine in acetic acid, dropwisely adding an acetic anhydride acetic acid solution, and carrying out selective acylation reaction to obtain 2-acetamido-4-amino-6-hydroxy-5-formamido pyrimidine; carrying out cyclization reaction on 2-acetamido-4-amino-6-hydroxy-5-formamido pyrimidine under the action of a catalyst A to obtain 2-acetamido-6-hydroxypurine; subjecting 2-acetamido-6-hydroxypurine to an acylation reaction in an acetic anhydride and acetic acid mixed solvent under the action of a catalyst C, and obtaining N(2),9-diacetyl guanine. Compared with a traditional process, the synthesis process has the advantages that a large amount of water is not introduced, a large amount of inorganic salt is not generated, used solvents can be recycled, the process is simple and convenient to operate, the productyield is slightly higher than that in the prior art, and the quality meets the corresponding quality standard.

Synthesis of Lipophilic Guanine N-9 Derivatives: Membrane Anchoring of Nucleobases Tailored to Fatty Acid Vesicles

Covalent or noncovalent surface functionalization of soft-matter structures is an important tool for tailoring their function and stability. Functionalized surfaces and nanoparticles have found numerous applications in drug delivery and diagnostics, and new functionalization chemistry is continuously being developed in the discipline of bottom-up systems chemistry. The association of polar functional molecules, e.g., molecular recognition agents, with soft-matter structures can be achieved by derivatization with alkyl chains, allowing noncovalent anchoring into amphiphilic membranes. We report the synthesis of five new guanine-N9 derivatives bearing alkyl chains with different attachment chemistries, exploiting a synthesis pathway that allows a flexible choice of hydrophobic anchor moiety. In this study, these guanine derivatives were functionalized with C10 chains for insertion into decanoic acid bilayer structures, in which both alkyl chain length and attachment chemistry determined their interaction with the membrane. Incubation of these guanine conjugates, as solids, with a decanoic acid vesicle suspension, showed that ether- and triazole-linked C10 anchors yielded an increased partitioning of the guanine derivative into the membranous phase compared to directly N-9-linked saturated alkyl anchors. Decanoic acid vesicle membranes could be loaded with up to 5.5 mol % guanine derivative, a 6-fold increase over previous limits. Thus, anchor chemistries exhibiting favorable interactions with a bilayer's hydrophilic surface can significantly increase the degree of structure functionalization.

Formation of the N2-acetyl-2,6-diaminopurine oligonucleotide impurity caused by acetyl capping

The acetyl 'capping' reaction routinely employed during phosphorothioate oligonucleotide synthesis has been implicated in the formation of an impurity species with a mass 41 amu greater than the expected oligonucleotide molecule. The impurity has been found to arise by conversion of a protected guanine nucleobase to N2-acetyl-2,6-diaminopurine. A two-part mechanism is proposed consisting of transamidation of the protecting group on guanine and substitution of guanine's O6 atom.

New 7-methylguanine derivatives targeting the influenza polymerase PB2 cap-binding domain

The heterotrimeric influenza virus polymerase performs replication and transcription of viral RNA in the nucleus of infected cells. Transcription by "cap-snatching" requires that host-cell pre-mRNAs are bound via their 5′ cap to the PB2 subunit. Thus, the PB2 cap-binding site is potentially a good target for new antiviral drugs that will directly inhibit viral replication. Docking studies using the structure of the PB2 cap-binding domain suggested that 7-alkylguanine derivatives substituted at position N-9 and N-2 could be good candidates. Four series of 7,9-di- and 2,7,9-trialkyl guanine derivatives were synthesized and evaluated by an AlphaScreen assay in competition with a biotinylated cap analogue. Three synthesized compounds display potent in vitro activity with IC50 values lower than 10 μM. High-resolution X-ray structures of three inhibitors in complex with the H5N1 PB2 cap-binding domain confirmed the binding mode and provide detailed information for further compound optimization.

Dynamers at the solid-liquid interface: Controlling the reversible assembly/reassembly process between two highly ordered supramolecular guanine motifs

(Figure Presented) String quartet: A dynamic assembly/reassembly process in octadecyl guanine (G) monolayers was triggered by addition of [2.2.2]cryptand, potassium picrate (K+(pic)-), and trifluoromethanesulfonic acid. The resulting structures, which alternate between a hydrogen-bonded G ribbon and a G quartet, were monitored by STM at the solid-liquid interface on graphite (see picture).

Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction

We have developed a practical synthesis of unique nucleoside derivatives via TiCl4 promoted multicomponent reaction of optically active dihydrofuran, ethyl pyruvate/glyoxylate, and a TMS protected nucleobase in a single-pot operation.

Guanine-Containing DNA Minor-Groove binders

Solid-phase procedures have been used to prepare six di-pyrrole-containing DNA ligands that combine (guanin-9-yl)-acetyl, (guanin-7-yl)acetyl or acetyl moieties at the N-terminal end and two lysines or a (dimethylamino)propyl group at the C terminus. Inspection of their DNA-stabilizing properties by UV-monitored thermal denaturation experiments showed that the ligand incorporating the (guanin-9-yl)acetyl group and the (dimethylamino)propyl tail had the highest duplex-stabilizing effects. Wiley-VCH Verlag GmbH & Co, KGaA.