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Description
2-Fluoroadenine, supplied under TCI catalogue code F0647, is a purine analogue derived from adenine in which a fluorine atom is bonded to the two position of the purine ring. The compound occupies an important place in nucleoside chemistry and medicinal chemistry, since adenine itself is one of the nitrogenous bases that make up nucleic acids. By replacing a single hydrogen atom on the purine ring with fluorine, researchers obtain a modified base that can be used to construct analogue nucleosides and nucleotides. The material is widely employed as a starting building block in the synthesis of purine-based active compounds and in biochemical studies of nucleic acids in research laboratories.
The property that gives this compound its high value is the influence the fluorine atom exerts on the behaviour of the purine ring. Fluorine at the two position provides an electron-withdrawing effect that alters the basicity of the ring and the hydrogen bonding pattern of the base, while at the same time conferring resistance to the enzymatic degradation pathways that normally attack adenine. Because the size of a fluorine atom is very close to that of hydrogen, the change in molecular shape is extremely small, so the resulting analogue is still recognised by biological systems even though its chemical behaviour has already changed. This combination of minimal steric disturbance and substantial electronic modification is the principle that makes fluorinated purines so useful to synthetic chemists.
In Indonesian laboratories, 2-Fluoroadenine is typically handled as a fine research-scale building block rather than a bulk reagent. It is most often found in university and institutional research groups working on nucleoside chemistry, in medicinal chemistry programmes exploring purine scaffolds, and in biochemistry laboratories investigating nucleic acid behaviour. Quantities are usually modest, reactions are run on a small scale, and the material is stored alongside other sensitive organic building blocks in a controlled chemical store.
Laboratory Applications
Synthesis of analogue nucleosides, where the fluorinated purine serves as the base component that is coupled to a sugar unit to produce modified nucleosides for further chemical study.
Preparation of nucleotide analogues for nucleic acid research, taking advantage of the altered hydrogen bonding pattern that fluorine substitution introduces into the purine base.
Medicinal chemistry exploration of purine scaffolds, where researchers use this building block to construct libraries of purine-based active compounds for structure and activity investigations.
Biochemical studies of enzymatic stability, since the fluorine substituent confers resistance to the degradation pathways that normally act upon unmodified adenine in biological systems.
Fluorinated building block work in general synthetic chemistry, where the near-identical size of fluorine and hydrogen allows the electronic character of a purine ring to be tuned without significant steric change.
Specifications
Brand: TCI
Catalogue code: F0647
CAS number: 700-49-2
Chemical name: 2-Fluoroadenine
Category: Chemistry > Building Blocks > Fluorinated Building Blocks
Storage: store as indicated on the manufacturer label and product documentation
Handling and Storage
Store 2-Fluoroadenine in its original tightly closed container, following the storage conditions stated on the manufacturer label and the accompanying product documentation. Keep the container in a cool, dry and well ventilated chemical store, away from direct sunlight, moisture and incompatible materials. As with all fine organic building blocks, handle the material in a fume hood using appropriate personal protective equipment, including gloves, safety glasses and a laboratory coat. Weigh out only the quantity required, close the container promptly afterwards to limit exposure to atmospheric moisture, and consult the safety data sheet supplied with the product before first use and before disposal.
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