Archaeosine

Archaeosine (/kjuːiːn/) (G*) is a modified nucleobase found in the dihydrouracil loop at position 15 of tRNAs found in Archaea,[1] and is thought to be important for the heat resistance of thermophilic archaea such as Thermococcus kodakarensis.[2][3][4]

Archaeosine

Names
IUPAC name 2-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carboximidamide
Other names 7-formamidino-7-deazaguanosine
Identifiers
CAS Number	148608-52-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:73271
ChemSpider	117239
PubChem CID	135718450
InChI InChI=1S/C12H16N6O5/c13-8(14)3-1-18(9-5(3)10(22)17-12(15)16-9)11-7(21)6(20)4(2-19)23-11/h1,4,6-7,11,19-21H,2H2,(H3,13,14)(H3,15,16,17,22)/t4-,6-,7-,11-/m1/s1 Key: PEMQXWCOMFJRLS-RPKMEZRRSA-N
SMILES C1=C(C2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(NC2=O)N)C(=N)N
Properties
Chemical formula	C12H16N6O5
Molar mass	324.297 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• Queuine

References

1. Kilpatrick MW, Walker RT (September 1981). "The nucleotide sequence of the tRNAMMet from the archaebacterium Thermoplasma acidophilum". Nucleic Acids Research. 9 (17): 4387–90. doi:10.1093/nar/9.17.4387. PMC 327441. PMID 6913864.
2. McCarty RM, Bandarian V (August 2012). "Biosynthesis of pyrrolopyrimidines". Bioorganic Chemistry. 43: 15–25. doi:10.1016/j.bioorg.2012.01.001. PMC 4022189. PMID 22382038.
3. Lorenz C, Lünse CE, Mörl M (April 2017). "tRNA Modifications: Impact on Structure and Thermal Adaptation". Biomolecules. 7 (2). doi:10.3390/biom7020035. PMID 28375166.
4. Turner B, Burkhart BW, Weidenbach K, Ross R, Limbach PA, Schmitz RA, et al. (March 2020). "Archaeosine Modification of Archaeal tRNA: Role in Structural Stabilization". Journal of Bacteriology. 202 (8). doi:10.1128/JB.00748-19. PMID 32041795.