Encyclopedia of Astrobiology

Living Edition
| Editors: Muriel Gargaud, William M. Irvine, Ricardo Amils, Henderson James Cleaves, Daniele Pinti, José Cernicharo Quintanilla, Michel Viso

p-RNA

  • Ramanarayanan KrishnamurthyEmail author
  • Eun-Kyong Kim
  • Tammy Campbell
Living reference work entry
DOI: https://doi.org/10.1007/978-3-642-27833-4_1277-3

Synonyms

Definition

Pyranosyl-RNA (“p-RNA”) is an oligonucleotide in which the ribose units exist in the pyranose form and are linked together repetitively by phosphodiester groups between the hydroxyl groups at positions C-2′ and C-4′ (Fig. 1).

Keywords

Watson-Crick Pentopyranosyl Oligonucleotides Nucleic acids Homochiral Heterochiral Base-pairing 
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References and Further Reading

  1. Beier F, Reck F, Wagner T, Krishnamurthy R, Eschenmoser A (1999) Chemical etiology of nucleic acid structure: comparing pentopyranosyl-(2′→4′) oligonucleotides with RNA. Science 283:699–703CrossRefADSGoogle Scholar
  2. Bolli M, Micura R, Eschenmoser A (1997a) Pyranosyl-RNA: chiroselective self-assembly of base sequences by ligative oligomerization of tetra nucleotide-2′,3′-cyclophosphates (with a commentary concerning the origin of biomolecular homochirality). Chem Biol 4:309–320CrossRefGoogle Scholar
  3. Bolli M, Micura R, Pitsch S, Eschenmoser A (1997b) Pyranosyl-RNA: further observations on replication. Helv Chim Acta 80:1901–1951CrossRefGoogle Scholar
  4. Eschenmoser A (1993a) Hexose nucleic acids. Pure Appl Chem 65:1179–1188, Lecture at the ‘18th IUPAC Symposium on the Chemistry of Natural Products’, Strasbourg/F, August 1992CrossRefGoogle Scholar
  5. Eschenmoser A (1993b) Toward a chemical etiology of the natural nucleic acids’ structure. In: Proc R. A. Welch Found, 37. Conf chem res 40 years of the DNA double Helix. R. A. Welch Foundation, Houston, p 201–235Google Scholar
  6. Eschenmoser A (1997) Towards a chemical etiology of nucleic acid structure. Orig Life Evol Biosph 27:535–553CrossRefADSGoogle Scholar
  7. Eschenmoser A (1999) Chemical etiology of nucleic acid structure. Science 284:2118–2124CrossRefGoogle Scholar
  8. Eschenmoser A (2011) Etiology of potentially primordial biomolecular structures: from vitamin B12 to the nucleic acids and an inquiry into the chemistry of life’s origin: a retrospective. Angew Chem Int Ed 50:12412–12472CrossRefGoogle Scholar
  9. Hamon C, Brandstetter T, Windhab N (1999) Pyranosyl-RNA supramolecules containing non-hydrogen bonding base-pairs. Synlett S1:940–944Google Scholar
  10. Huang Y, Light J (II), Mather E, Weisburg W (2010) Methods for detecting nucleic acids in a sample. Patent No. US 2010/0167294 A1Google Scholar
  11. Jungmann O, Wippo H, Stanek M, Huynh HK, Krishnamurthy R, Eschenmoser A (1999) Promiscuous Watson−Crick cross-pairing within the family of pentopyranosyl (4′→2′) oligonucleotides. Org Lett 1:1527–1530CrossRefGoogle Scholar
  12. Krishnamurthy R, Pitsch S, Minton M, Miculka C, Windhab N, Eschenmoser A (1996) Pyranosyl-RNA: base pairing between homochiral oligonucleotide strands of opposite sense of chirality. Angew Chem Int Ed 35:1537–1541CrossRefGoogle Scholar
  13. Micura R, Bolli M, Windhab N, Eschenmoser A (1997) Pyranosyl-RNA also forms hairpin structures. Angew Chem Int Ed 36:870–873CrossRefGoogle Scholar
  14. Pitsch S, Wendeborn S, Jaun B, Eschenmoser A (1993) Why pentose- and not hexose-nucleic acids? Pyranosyl-RNA (‘p-RNA’). Helv Chim Acta 76:2161–2183CrossRefGoogle Scholar
  15. Pitsch S, Pombo-Villar E, Eschenmoser A (1994) Chemistry of alpha-aminonitriles. Formation of 2-oxoethyl phosphates (glycolaldehyde phosphates) from rac-oxiranecarbonitrile and on (formal) constitutional relationships between 2-oxoethyl phosphates and oligo(hexo- and pentopyranosyl)nucleotide backbones. Helv Chim Acta 77:2251–2285CrossRefGoogle Scholar
  16. Pitsch S, Krishnamurthy R, Bolli M, Wendeborn S, Holzner A, Minton M, Lesueur C, Schlonvogt I, Jaun B, Eschenmoser A (1995) Pyranosyl-RNA (‘p-RNA’): base-pairing selectivity and potential to replicate. Helv Chim Acta 78:1621–1635CrossRefGoogle Scholar
  17. Pitsch S, Wendeborn S, Krishnamurthy R, Holzner A, Minton M, Bolli M, Miculka C, Windhab N, Micura R, Stanek M, Jaun B, Eschenmoser A (2003) The β-D-ribopyranosyl-(4′→2′)-oligonucleotide system (pyranosyl-RNA): synthesis and resumé of base-pairing properties. Helv Chim Acta 86:4270–4363CrossRefGoogle Scholar
  18. Preparata F P, Upfal E, Oliver J S (2003) Systems and methods for sequencing by hybridization. Patent No. US 2003/0064382 A1Google Scholar
  19. Schlönvogt I, Pitsch S, Lesueur C, Eschenmoser A (1996) Pyranosyl-RNA (‘p-RNA’): NMR and molecular-dynamics study of the duplex formed by self-pairing of ribopyranosyl-(C-G-A-A-T-T-C-G). Helv Chim Acta 79:2316–2345CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg (outside the USA) 2014

Authors and Affiliations

  • Ramanarayanan Krishnamurthy
    • 1
    Email author
  • Eun-Kyong Kim
    • 1
  • Tammy Campbell
    • 1
  1. 1.ChemistryThe Scripps Research InstituteLa JollaUSA