Synonyms
Keywords
Base-pairing, heterochiral, homochiral, nucleic acid, oligonucleotides, pentopyranose, Watson–Crick
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).
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References and Further Reading
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 283:699–703
Bolli M, Micura R, Pitsch S, Eschenmoser A (1997a) Pyranosyl-RNA: further observations on replication. Helv Chim Acta 80:1901–1951
Bolli M, Micura R, Eschenmoser A (1997b) 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 4:309–320
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 1992)
Eschenmoser A (1993b) Toward a chemical etiology of the natural nucleic acids’ structure. In: Proceedings of the Robert A. Welch foundation 37th conference on chemical research 40 years of the DNA double helix. Robert A. Welch Foundation, Houston, TX, USA, 201–235
Eschenmoser A (1996) Towards a chemical etiology of the nucleic acids structure. Orig Life Evol Biosph 27:535–553
Eschenmoser A (1999) Chemical etiology of nucleic acid structure. Science 284:2118–2124
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 1:1527–1530
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 35:1537–1541
Micura R, Bolli M, Windhab N, Eschenmoser A (1997) Pyranosyl-RNA also forms hairpin structures. Angew Chem Int Ed 36:870–873
Pitsch S, Wendeborn S, Eschenmoser A (1993) Why pentose- and not hexose-nucleic acids? Pyranosyl RNA ‘p RNA’. Helv Chim Acta 76:2161–2183
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 77:2251–2285
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 78:1621–1635
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 86:4270–4363
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 79:2316–2345
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Krishnamurthy, R., Naidu, S.V., Punna, V. (2011). p-RNA. In: Gargaud, M., et al. Encyclopedia of Astrobiology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-11274-4_1277
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