Archaeosine

Archaeosine
Names
Preferred IUPAC name
7-Carbaguanosine-7-carboximidamide
Systematic IUPAC name
2-Amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboximidamide
Other names
7-formamidino-7-deazaguanosine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • 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
  • 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
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).

Archaeosine (G*), semi-systematic name 7-formamidino-7-deazaguanosine (fa7d7G), is a modified nucleoside found in the dihydrouracil loop at position 15 of tRNAs found in Archaea, and is thought to be important for the heat resistance of thermophilic archaea such as Thermococcus kodakarensis.

See also

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): 35. doi:10.3390/biom7020035. PMC 5485724. 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. PMC 7099136. PMID 32041795.