First experimental evidence for the preferential stabilization of the natural D- over the nonnatural L-configuration in nucleic acids

RNA

Volumn 13, Issue 11, 2007, Pages 1877-1880

  Bolik, Sarah ^a   Rübhausen, Michael ^a   Binder, Stephan ^a   Schulz, Benjamin ^a   Perbandt, Markus ^a   Genov, Nicolay ^b   Erdmann, Volker ^c   Klussmann, Sven ^d   Betzel, Christian ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

^d NOXXON PHARMA AG   (Germany)

Author keywords

Enantiomer; Homochirality; Raman spectroscopy; RNA stabilization; Stereoselection

Indexed keywords

NUCLEIC ACID; RIBOSE;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; RAMAN SPECTROMETRY; RNA SEQUENCE; RNA STABILITY; SEQUENCE ANALYSIS; STEREOCHEMISTRY;

NUCLEIC ACID CONFORMATION; OLIGORIBONUCLEOTIDES; RNA; SPECTRUM ANALYSIS, RAMAN; STEREOISOMERISM; THERMODYNAMICS;

EID: 35548929411     PISSN: 13558382     EISSN: 14699001     Source Type: Journal    
DOI: 10.1261/rna.564507     Document Type: Article

References (21)

1. Bonner, W.A. 1999. Enantioselective autocatalysis. V. The spontaneous resolution of tri-O-thymotide. Orig. Life Evol. Biosph. 29: 317-328.
2. Cech, T. 1989. Ribozyme self-replication? Nature 339: 507-508.
3. Cordova, A., Ibrahem, I., Casas, J., Sunden, H., Engqvist, M., and Reyes, E. 2005a. Amino acid catalyzed neogenesis of carbohydrates: A plausible ancient transformation. Chemistry 11: 4772-4784.
4. Cordova, A., Enqvist, M., Ibrahem, I., Casas, J., and Sunden, H. 2005b. Plausible origins of homochirality in the amino acid catalyzed neogenesis of carbohydrates. Chem. Commun. 20: 2047-2049.
5. Davankov, V. 2006. Chirality as an inherent general property of matter. Chirality 18: 459-461.
6. Faglioni, F., Passalacqua, A., and Lazzeretti, P. 2005. Parity violation energy of biomolecules. I: Polypeptides. Orig. Life Evol. Biosph. 35: 461-475.
7. Hazen, R., Filley, T., and Goodfriend, G. 2001. Selective adsorption of L- and D-amino acids on calcite: Implications for biochemical homochirality. Proc. Natl. Acad. Sci. 98: 5487-5490.
8. Kondepudi, D.K. and Nelson, G.W. 1985. Weak neutral currents and the origin of biomolecular chirality. Nature 314: 438-441.
9. Meierhenrich, U. and Thiemann, W. 2004. Photochemical concepts on the origin of biomolecular asymmetry. Orig. Life Evol. Biosph. 34: 111-121.
10. Nanita, S. and Cooks, R. 2006. Serine octamers: Cluster formation, reactions, and implications for biomolecule homochirality. Angew. Chem. Int. Ed. Engl. 45: 554-569.
11. Perbandt, M., Vallazza, M., Lippmann, C., Betzel, Ch., and Erdmann, V.A. 2001. Structure of an RNA duplex with an unusual G·C pair in wobble-like conformation at 1.6 Å resolution. Acta Crystallogr. D Biol. Crystallogr. 57: 219-224.
12. Schulz, B., Bäckström, J., Budelmann, D., Maeser, R., Rübhausen, M., Klein, M.V., Schoeffel, E., Mihill, A., and Yoon, S. 2005. Fully reflective deep ultraviolet to near infrared spectrometer and entrance optics for resonance Raman spectroscopy. Rev. Sci. Instrum. 76: 1-12.
13. Tamura, K. and Schimmel, P.R. 2006. Chiral-selective aminoacylation of an RNA minihelix: Mechanistic features and chiral suppression. Proc. Natl. Acad. Sci. 103: 13750-13752.
14. Tranter, G.E. 1985. The parity violating energy differences between the enantiomers of α-amino acids. Mol. Phys. 56: 825-838.
15. Tranter, G.E. 1987. The enantio-preferential stabilization of D-ribose from parity violation. Chem. Phys. Lett. 135: 279-282.
16. Urata, H. 1999. Effect of chirality of ribose on nucleic acid structure and function. Yakugaku Zasshi 119: 689-709.
17. Urata, H., Sasaki, R., Morita, H., Kusumoto, M., Ogawa, Y., Mitsuda, K., and Akagi, M. 2005. Kinetic analysis of hydrolytic reaction of homo- and heterochiral adenylyl (3′-5′) adenosine isomers: Breaking homochirality reduces hydrolytic stability of RNA. Chem. Commun. 20: 2578-2580.
18. Vallazza, M., Perbandt, M., Klussmann, S., Rypniewski, W., Einspahr, H.M., Erdmann, V.A., and Betzel, Ch. 2004. First look at RNA in-L-configuration. Acta Crystallogr. D Biol. Crystallogr. 60: 1-7.
19. Wolfrom, M., Lemieux, R., and Olin, S. 1949. Configurational correlation of L-(levo)-glyceraldehyde with natural (dextro)-alanine by a direct chemical method. J. Am. Chem. Soc. 71: 2870-2873.
20. Yamagata, Y. 1966. A hypothesis for the asymmetric appearance of biomolecules on Earth. J. Theor. Biol. 11: 495-498.
21. Zaug, A. and Cech, T. 1986. The intervening sequence RNA of tetrahymena is an enzyme. Science 231: 470-475.