Pyranosyi-RNA: Chiroselective self-assembly of base sequences by ligative oligomerization of tetranucleotide-2',3'-cyclophosphates (with a commentary concerning the origin of biomolecular homochirality)

Chemistry and Biology

Volumn 4, Issue 4, 1997, Pages 309-320

  Bolli, Martin ^a,b   Micura, Ronald ^a   Eschenmoser, Albert ^a,b  

^a ETH ZURICH   (Switzerland)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

biomolecular homochirality; chiroselectivity; oligonucleotides; pyranosyl RNA; self assembly

Indexed keywords

BIOPOLYMER; OLIGORIBONUCLEOTIDE; RIBOSE; RNA;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; STEREOISOMERISM;

BIOPOLYMERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; OLIGORIBONUCLEOTIDES; RIBOSE; RNA; STEREOISOMERISM;

EID: 0030611061     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(97)90074-0     Document Type: Article

References (31)

1. Eschenmoser, A. (1993). Hexose nucleic acids. Pure Appl. Chem. 65, 1179-1188.
2. Pitsch, S., Wendeborn, S., Jaun, B. & Eschenmoser, A. (1993). Why pentose- and not hexose-nucleic acids? Pyranosyl-RNA ('p-RNA'). Helv. Chim. Acta 76, 2161-2183.
3. Pitsch, S., et al., & Eschenmoser, A. (1995). Pyranosyl-RNA ('p-RNA'): base-pairing selectivity and potential to replicate. Helv. Chim. Acta 78, 1621-1635.
4. 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. Engl. 35, 1537-1541.
5. Schlönvogt, I., Pitsch, S., Lesueur, C., Eschenmoser, A., Jaun, B. & Wolf, R.M. (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.
6. Micura, R., Bolli, M., Windhab, N. & Eschenmoser, A. (1997). Pyranosyl-RNA also forms hairpin structures. Angew. Chem. Int. Ed. Engl., in press.
7. Eschenmoser, A. (1993). 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', pp. 201-235, The Robert A. Welch Foundation, Housten, Texas, USA.
8. Fischer, R.W. (1992). Allopyranosyl-Nukleinsäure: synthese, Paarungseigenschaften und struktur von adenin-/uracil-haltigen oligonukleotiden. [Allopyranosyl nucleic acid: synthesis, pairing properties and and structure of adenine-/uracil-containing oligonucleotides]. Thesis No. 9971, ETH Zürich.
9. Helg, A.G. (1994). Allopyranosyl-nukleinsäure: synthese, Paarungseigenschaften und struktur von guanin/cytosin-enthaltenden oligonukleotiden. [Allopyranosyl nucleic acid: synthesis, pairing properties and structure of guanine/cytosine-containing oligonucleotides]. Thesis No. 10464, ETH Zürich.
10. Diederichsen, U. (1993). Hypoxanthin-basenpaarungen in homo-DNA-oligonucleotiden; zur frage des paarungsverhaltens von glucopyranosyl-oligonucleotiden. [Basepairs involving hypoxanthine in homo-DNA oligonucleotides; concerning the basepairing in glucopyranosyl oligonucleotides]. Thesis No. 10122, ETH Zürich.
11. Groebke, K. (1993). Über purin-purin-paarungen bei hexopyranosenukleinsäuren. [Purine-purine pairing in hexopyranose nucleic acids]. Thesis No. 10149, ETH Zürich.
12. Eschenmoser, A. (1991). Warum pentose- und nicht hexosenucleinsäuren? [Why pentose and not hexose nucleic acids?]. Nachr. Chem. Tech. Lab. 39, 795-806.
13. Hunziker, J., et al., & Eschenmoser, A. (1993). Warum pentose- und nicht hexose-nucleinsäuren? Teil III. Oligo(2′,3′-dideoxy-β-D-glucopyranosyl)nucleotide ('homo-DNS'): Paarungseigenschaften. [Why pentose and not hexose nucleic acids? Part III. Oligo(2′,3′-dideoxy-β-D-glucopyranosyl)nucleotides ('homo-DNA'): pairing properties.] Helv. Chim. Acta 76, 259-352.
14. Orgel, L.E. (1992). Molecular replication. Nature 358, 203-209.
15. Joyce, G.F., Visser, G.M., Van Boeckel, C.A.A., van Boom, J.H., Orgel, L.E. & van Westrenen, J. (1984). Chiral selection in poly(C)-directed synthesis of oligo(G). Nature 310, 602-604.
16. Renz, M., Lohrmann, R. & Orgel, L.E. (1971). Catalysts for the polymerization of adenosine cyclic 2′,3′-phosphate on a poly (U) template. Biochim. Biophys. Acta 240, 463-471.
17. Usher, D.A. (1972). RNA double helix and the evolution of the 3′,5′ linkage. Nature (New Biology) 235, 207-208.
18. Usher, D.A. & McHale, A.H. (1976). Hydrolytic stability of helical RNA: a selective advantage for the natural 3′,5′-bond. Proc. Natl Acad, Sci. USA 73, 1149-1153.
19. Bonner, WA (1991). The origin and amplification of biomolecular chirality. Orig. Life Evol. Biosphere 21, 59-111.
20. Ertem, G. & Ferris, J.P. (1996). Synthesis of RNA oligomers on heterogeneous templates. Nature (London, UK) 379, 238-240.
21. Ferris, J.P., Hill Jr., A.R., Liu, R. & Orgel, L.E. (1996). Synthesis of long prebiotic oligomers on mineral surfaces. Nature 381, 59-61.
22. Strong, W.M. (1898). (Letter to the Editor). Nature 59, 53-54.
23. Kuhn, H. (1972). Self-organization of molecular systems and evolution of the genetic apparatus. Angew. Chem. Int. Ed. Engl. 11, 798-820.
24. Kuhn, H. & Waser, J. (1981). Molecular self-organization and the origin of life. Angew. Chem. Int. Ed. Engl. 20, 500-520.
25. Green, M.M. & Garetz, B.A. (1984). The configurational stereochemistry of atactic vinyl homopolymers. Tetrahedron Lett. 25, 2831-2834.
26. Avetisov, V. & Goldanskii, V. (1996). Mirror symmetry breaking at the molecular level. Proc. Natl. Acad. Sci. USA 93, 11435-11442.
27. Mason, S.F. & Tranter, G.E. (1985). The electroweak origin of biomolecular handedness. Proc. R. Soc. Lond. A 397, 45-65.
28. Mason, S.F. (1984). Origins of biomolecular handedness. Nature 311, 19-23.
29. Eigen, M. & Winkler, R. (1975). Das spiel, p. 145, R. Piper & Co. Verlag, München.
30. Orgel, L.E. (1973). The origins of life. In Molecules and Natural Selection. J. p. 167, Wiley & Sons, N.Y., USA.
31. Cronin, J.R. & Pizzarello, S. (1997). Enantiomeric excesses in meteoritic amino acids. Science 275, 951-955.