Chemical Etiology of Nucleic Acid Structure: Comparing Pentopyranosyl-(2'→4') Oligonucleotides with RNA

Author:

Beier M.1,Reck F.1,Wagner T.1,Krishnamurthy R.1,Eschenmoser A.1

Affiliation:

1. The Skaggs Institute for Chemical Biology at The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, and Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule (ETH), Universitätstrasse 16, CH-8092 Zürich, Switzerland.

Abstract

All four members of the family of pentopyranosyl-(2′→4′) oligonucleotide systems that contain β-ribo-, β-xylo-, α-lyxo-, or α-arabinopyranosyl units as repeating sugar building blocks are found to be much stronger Watson-Crick base-pairing systems than RNA. The α-arabinopyranosyl system is the strongest of all and in fact belongs to the strongest oligonucleotide base-pairing systems known. Whatever the chemical determinants by which nature selected RNA as a genetic system, maximization of base-pairing strengths within the domain of pentose-derived oligonucleotide systems was not the critical selection criterion.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Reference65 articles.

1. A. Eschenmoser in Verh. Ges. Dtsch. Naturforsch. Aerzte 116 135 (1990);

2. ___, Dobler M., Helv. Chim. Acta 75, 218 (1992);

3. Eschenmoser A., Loewenthal E., Chem. Soc. Rev. 21, 1 (1992);

4. ; A. Eschenmoser in Proc. Robert A. Welch Found. Conf. Chem. Res. 37 (Robert A. Welch Foundation Houston TX 1993) p. 201.

5. The closest structural alternative to RNA that satisfies this criterion is the RNA isomer containing (2′→5′)- instead of the (3′→5′)-phosphodiester junctions. For studies on this system in the etiological context see

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