3-deaza-2'-deoxyadenosine, 3-deaza-dA
3-Deaza-2'-Deoxyadenosine (3-Deaza-dA) is a modified purine nucleoside analog in which the nitrogen atom at the 3-position of the adenine ring is replaced with a carbon atom. Although this modification preserves the overall structure of adenine and its ability to form standard Watson-Crick base pairs with thymine, it alters the electronic properties of the purine ring and removes a potential hydrogen-bond acceptor. These changes make 3-Deaza-dA an important tool for studying nucleic acid structure, molecular recognition, and enzyme-substrate interactions.
Because the modification is located within the heterocyclic base rather than the sugar or phosphate backbone, oligonucleotides containing 3-Deaza-2'-deoxyadenosine generally maintain native duplex geometry while exhibiting altered interactions with DNA-binding proteins, polymerases, and repair enzymes. Researchers frequently incorporate this analog to investigate the contribution of specific purine nitrogen atoms to DNA stability, protein recognition, and catalytic mechanisms.
In synthetic biology and nucleic acid chemistry, 3-Deaza-dA provides a valuable approach for probing hydrogen-bonding networks without introducing major steric changes. This allows systematic evaluation of base-specific interactions while minimizing disruption of the DNA duplex.
Typical applications include:
- DNA structure and stability studies
- DNA-protein interaction analysis
- DNA polymerase fidelity studies
- Restriction enzyme recognition studies
- DNA repair mechanism research
- Structural biology
- Nucleic acid chemistry
- Synthetic biology
- Aptamer engineering
- Mechanistic enzymology
Bio-Synthesis offers 3-Deaza-2'-Deoxyadenosine phosphoramidite for incorporation into custom DNA oligonucleotides at user-defined positions. The modification is compatible with standard solid-phase DNA synthesis and can be combined with numerous additional modifications, including fluorophores, quenchers, biotin, amino modifiers, thiol modifiers, click chemistry handles, PEG linkers, and other custom conjugates.
Each oligonucleotide is synthesized using optimized phosphoramidite chemistry and is available with optional desalting, HPLC purification, or PAGE purification, together with analytical characterization by LC-MS, MALDI-TOF, capillary electrophoresis, and additional quality control testing as required.
The minimal structural perturbation introduced by 3-Deaza-2'-Deoxyadenosine makes it an excellent choice for researchers investigating the molecular basis of DNA recognition, enzyme catalysis, and nucleic acid function while preserving the native architecture of the DNA duplex.
| Property |
Typical Value |
| Modification |
3-Deaza-2'-Deoxyadenosine (3-Deaza-dA) |
| Base Analog |
Adenine analog |
| Structural Change |
N3 replaced by carbon |
| Base Pairing |
Pairs with thymine (T) |
| Sugar |
2'-Deoxyribose |
| Compatible Oligos |
DNA and chimeric DNA/RNA oligonucleotides |
| Typical Applications |
DNA structure studies, protein binding, enzyme recognition, synthetic biology |
Product Information
3-deaza-2'-deoxyadenosine, 3-deaza-dA
-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at -20°C) in a nuclease-free environment should be stable for years.
References/Citations:
- Seela F, et al. Synthesis and properties of deazapurine nucleosides and oligonucleotides. Nucleosides, Nucleotides & Nucleic Acids.
- Herdewijn P. Modified Nucleosides in Biochemistry, Biotechnology and Medicine. Wiley-VCH.
- Blackburn GM, Gait MJ, Loakes D, Williams DM. Nucleic Acids in Chemistry and Biology. 3rd ed. Royal Society of Chemistry.
- Crooke ST. Antisense Drug Technology: Principles, Strategies, and Applications. 2nd ed. CRC Press.
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