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Description
TCI D4324 7-Deazahypoxanthine is an analogue of hypoxanthine in which the nitrogen atom at position 7 of the purine ring has been replaced by a carbon atom, giving a pyrrolo[2,3-d]pyrimidinone framework. This compound is an important heterocyclic building block in nucleoside and nucleotide chemistry, because it preserves the overall shape of the natural purine base while removing one hydrogen-bond acceptor point. In the laboratory, the material serves as a starting material for the synthesis of 7-deazapurine nucleosides, modified oligonucleotide probes, and test compounds in enzyme research involving purine bases.
The property that makes it so widely chosen is its very close structural resemblance to hypoxanthine, combined with a meaningful electronic change. Replacing N7 with CH strengthens the aromatic character of the five-membered ring, alters basicity and tautomeric patterns, and opens position 7 to functionalisation through halogenation or cross-coupling reactions — something that is not possible with the natural purine. Nucleosides built from it are also generally more resistant to glycosidic bond hydrolysis, making them suitable for probes and analogues that require higher stability in aqueous media.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on synthetic organic chemistry, nucleoside chemistry, and molecular biology reagent development. It is normally handled on a small synthetic scale as a starting material for multi-step routes toward modified bases and probes. Researchers preparing enzyme assay substrates or oligonucleotide modifications rely on it where a purine-shaped scaffold with an addressable position 7 is required.
Laboratory Applications
Synthesis of 7-deazapurine nucleosides, where the carbon at position 7 provides a stable, functionalisable site that natural purine bases cannot offer to the synthetic chemist.
Preparation of modified oligonucleotide probes, since nucleosides derived from this base resist glycosidic bond hydrolysis and remain more stable in aqueous working media.
Enzyme research using purine bases, where the removal of one hydrogen-bond acceptor point allows recognition and binding requirements to be probed systematically.
Halogenation and cross-coupling chemistry at position 7, giving access to substituted analogues through routes that are simply unavailable on the natural purine scaffold.
Structure–activity studies in nucleoside chemistry, because the compound keeps the overall shape of hypoxanthine while introducing a defined and meaningful electronic change.
Specifications
Brand: TCI
CAS number: 3680-71-5
Chemical name: 7-Deazahypoxanthine (pyrrolo[2,3-d]pyrimidinone framework)
Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
Product code: D4324
Pack sizes: available in research-scale packaging; please refer to the current catalogue listing for available sizes
Storage: store according to the manufacturer's label and the accompanying safety data sheet
Handling and Storage
Store the material in its original tightly closed container, in a cool, dry and well-ventilated area away from direct sunlight, moisture and incompatible materials, following the storage conditions stated on the manufacturer's label and safety data sheet. Keep the container sealed when not in use to limit exposure to atmospheric moisture. Handle in a fume hood using standard laboratory personal protective equipment, including safety glasses, gloves and a laboratory coat. Weigh and transfer using clean, dry spatulas and glassware to avoid cross-contamination, and allow the container to reach room temperature before opening if it has been kept refrigerated. Dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.
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