2'-Deoxyguanosine 3'-monophosphate sodium salt

• CAS: 102814-03-9
• Catalog Number: ACM102814039
• Category: Main Products
• Molecular Weight: 391.19
• Molecular Formula: C₁₀H₁₂N₅O₇P·2Na
• Synonyms: 2-Deoxyguanosine-3-Monophosphate; 2-DEOXYGUANOSINE 3-MONOPHOSPHATE SODIUM; 2-Deoxy-3-guanylic acid disodium salt
• IUPAC Name: disodium;[(2R,3S,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]phosphate
• Canonical SMILES: C1C(C(OC1N2C=NC3=C2NC(=NC3=O)N)CO)OP(=O)([O-])[O-].[Na+].[Na+]
• InChI Key: XCCLLAPCIBANDF-FVALZTRZSA-L
• Exact Mass: 369.04500
• Hazard Statements: Xi: Irritant
• Safety Description: 26-36

Case Study

Photoinduced Charge Transfer Dynamics in A Guanine and Thymine Dinucleotide Model

Duchi M, et al. Physical Chemistry Chemical Physics, 2019, 21(26), 14407-14417.

The main nonradiative relaxation dynamics of guanine and thymine model nucleotides (2'-deoxyguanosine 3'-monophosphate 5'-thymidine, d(GpT)) in buffered aqueous solutions were studied. Results show that the Franck-Condon excited state of d(GpT) is significantly delocalized at both nucleobases and mediates the d(G+ pT- ) exciplex product on ultrafast (<350 fs) time scales formation. Exciplexes rapidly convert back to the neutral ground state molecule on a time scale of ~10 ps with high quantum yield, ensuring the photostability of the nucleotide sequence.
Preparation of d(GpT)
· Using 2'-deoxyguanosine-5'-monophosphate disodium salt (>98%) and thymidine-5'-monophosphate disodium salt (>99%) as raw materials, standard phosphoramidite coupling and deprotection procedure for the preparation of 2'-deoxyguanosine 3'-monophosphate 5'-thymidine. The final compound was purified by preparative HPLC.
· For all reported spectroscopic studies, mono- and di-nucleotides were prepared at 10 mM concentration in D2O phosphate buffer solution (pD 7).

Application of 2'-Deoxyguanosine 3'-Monophosphate in the Synthesis of Guanine Quartets

Stefan L, et al. Nature Reviews Chemistry, 2019, 3(11), 650-668.

Guanine and related nucleobases such as guanosine, deoxyguanosine, and isoguanosine are well-known molecular tools for designing functional supramolecular assemblies. For example, 2'-deoxyguanosine-3'-monophosphate can be used to synthesize lipophilic and water-soluble G-quartets. Sherman and colleagues scrutinized the structure of tetrameric GMP, following the lipophilic TASQ approach and exploiting the phosphate group of the 2'-deoxyguanosine-3'-monophosphate to link guanines to the cavitand template.
Lipophilic versus water-soluble G-quartets
· LipoGs have been instrumental in understanding the factors that govern G-quartet formation and stability, thanks to the broad variety of techniques implementable in organic solvents.
· From a structural point of view, the simplest hydrophilic monomer is guanosine monophosphate. Early investigations on G-quartet formation were performed using concentrated GMP solutions (25mg·mL-1). The structure of GMP-based, hydrophilic G-quartets was further investigated later on, through modern analytical techniques.
· The presence of cations is not mandatory for the G-quartet formation of water-soluble TASQ; this new molecular tool was not exploited for cation chelation but as a DNA-mimicking platform to investigate the interactions between G-quartets and G4-ligands.