2'-Deoxyisoguanosine, IsodG

2'-Deoxyisoguanosine (isoG) is a non-natural purine nucleoside analog and an isomer of 2'-deoxyguanosine (dG) in which the amino and carbonyl functional groups are arranged differently on the purine ring. This altered hydrogen-bonding pattern gives isoG unique base-pairing properties that differ from those of natural guanine, making it a valuable building block for expanded genetic alphabets, synthetic biology, aptamer engineering, nucleic acid nanotechnology, and fundamental studies of DNA recognition and replication.

In oligonucleotides, 2'-deoxyisoguanosine can pair preferentially with isocytidine (isoC) through complementary hydrogen bonding, forming an orthogonal base pair that is distinct from the natural A:T and G:C base pairs. Under some conditions, isoG may also exhibit alternative pairing or tautomerization, which has been extensively studied in efforts to develop artificial genetic systems and investigate DNA polymerase fidelity.

Incorporation of isoG into synthetic DNA enables researchers to:

• Construct unnatural base pairs for expanded genetic alphabets.
• Study DNA replication fidelity and enzyme recognition.
• Design aptamers and functional nucleic acids with enhanced chemical diversity.
• Develop DNA nanostructures with orthogonal hybridization properties.
• Investigate molecular recognition and hydrogen-bonding mechanisms.
• Explore applications in synthetic biology, molecular computing, and directed evolution.

Bio-Synthesis offers 2'-deoxyisoguanosine phosphoramidite for incorporation into custom DNA oligonucleotides at defined sequence positions. The modification can be combined with a wide range of additional chemistries, including fluorophores, quenchers, biotin, amino modifiers, click chemistry handles, PEG linkers, and other custom conjugates, enabling highly specialized research applications.

Note: [i2dIsoG]  base is incorporated internally within the DNA sequence, not as a 5' or 3' terminal label.

Product Information

 

Product Name:

2'-Deoxyisoguanosine, IsodG

Alternate Name:

isoGuanosine (iso-dG) isoG

Modification Code:

[i2dIsoG]

Structure:

Purification:

HPLC

Delivery Format:

Lyophilized

Shipping Conditions:

Room Temperature

Storage Conditions:

-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:

Selected References

1. Switzer C, Moroney SE, Benner SA. Enzymatic incorporation of a new base pair into DNA and RNA. Journal of the American Chemical Society. 1989;111(21):8322–8323. https://doi.org/10.1021/ja00203a067
2. Benner SA, Sismour AM. Synthetic biology. Nature Reviews Genetics. 2005;6(7):533–543. https://doi.org/10.1038/nrg1637
3. Hoshika S, et al. Hachimoji DNA and RNA: A genetic system with eight building blocks. Science. 2019;363(6429):884–887. https://doi.org/10.1126/science.aat0971
4. Seela F, Ming X. Synthesis and base-pairing properties of 2'-deoxyisoguanosine-containing oligonucleotides. Nucleosides, Nucleotides & Nucleic Acids. (Representative work on isoG chemistry and hybridization.)

Note: Because 2'-deoxyisoguanosine can undergo tautomerization that may influence pairing behavior, oligonucleotides containing isoG are generally intended for research applications involving artificial base-pair systems rather than routine PCR or standard hybridization assays.

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