5-Aminouridine Chemical Properties

Melting point:

214-216 °C

Density 

1.712±0.06 g/cm3(Predicted)

storage temp. 

−20°C

pka

9.31±0.10(Predicted)

InChI

InChI=1S/C9H13N3O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2,10H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1

InChIKey

YBTWWWIJBCCYNR-UAKXSSHOSA-N

SMILES

OC[C@H]1O[C@@H](N2C=C(N)C(=O)NC2=O)[C@H](O)[C@@H]1O

Safety Information

WGK Germany 

3

5-Aminouridine Usage And Synthesis

Description

5-Aminouridine can modify nucleobases and can be incorporated into the target DNA. 5-Aminouridine exhibits a wide range of biological activity and it inhibits the growth of tumors, fungi and viruses.

in vitro

This modified nucleobase, 5-Aminouridine, must exhibit a low enough potential to be oxidized by Os(bpy)3³⁺. These modified nucleobases can be inserted into the target DNA by direct synthesis using modified phosphoramidites

in vivo

5-Aminouridine inhibits the incorporation of carbamyl aspartate into pyrimidines of both RNA and DNA in rat lived and [32P]phosphate into phospholipids and RNA nucleotides of rat liver slices and hepatoma. 5-Aminouridine was found to be incorporated into the RNA of Ehrlich ascites cells, and 5-aminouridine monophosphate was shown to be a strong inhibitor of orotidine 5'-phosphate decarboxylase[1].

References

[1] David A. Smith, Donald W. Visser, P. Roy-Burman. “Studies on 5-aminouridine.” Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis 119 2 (1966): Pages 221-228.