8-Azaguanosine Chemical Properties

Melting point:

250-252 °C (decomp)(Solv: water (7732-18-5))

Density 

2.49±0.1 g/cm3(Predicted)

pka

8.32±0.20(Predicted)

InChI

InChI=1/C9H12N6O5/c10-9-12-5-2(6(18)13-9)11-1-15(5)8-4(17)3(16)7(14-19)20-8/h1,3-4,7-8,14,16-17,19H,(H3,10,12,13,18)/t3-,4+,7-,8+/s3

InChIKey

DGHTWAQOVOJABA-BKVVLWDVNA-N

SMILES

ON[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)[C@H](O)[C@@H]1O |&1:2,4,16,18,r|

8-Azaguanosine Usage And Synthesis

Uses

8-Azaguanosine is an azapurine nucleoside.An extensive study has been made of the fluorescence emission properties of the neutral and ionic forms in aqueous medium of the 8-Azaguanosine. The 8-?azaguanosine is a substrate of purine nucleoside phosphorylase (PNP)?.

Definition

8-Azaguanosine (azaG) could replace specifically guanosine in the GpUpU codon for valine or the GpCpU codon for alanine in the stimulation of the binding of [14C]aminoacyl-tRNA to ribosomes. However, the binding efficiency in the presence of azaG-containing triplets was lower than in the presence of the natural codons. AzaG could replace guanosine in the 5'-position of codons for valine, alanine, and aspartic acid, as well as in the second position of codons for arginine. However, the template activity of azaG-containing triplets is lower than that of "normal" codons[1].

References

[1] D. Grünberger, F. ?orm, A. Holy?. “Synthesis and coding properties of 8-azaguanosinecontaining triribonucleoside diphosphates.” Biochimica et Biophysica Acta-Bioenergetics 31 1 (1968): 147–55.