Chemical Etiology of Nucleic Acid Structure: The α-Threofuranosyl-(3'→2') Oligonucleotide System

Author:

Schöning K.-U.1,Scholz P.1,Guntha S.1,Wu X.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, Universitätstrasse 16, CH-8092 Zürich, Switzerland.

Abstract

TNAs [( l )-α-threofuranosyl oligonucleotides] containing vicinally connected (3′→2′) phosphodiester bridges undergo informational base pairing in antiparallel strand orientation and are capable of cross-pairing with RNA and DNA. Being derived from a sugar containing only four carbons, TNA is structurally the simplest of all potentially natural oligonucleotide-type nucleic acid alternatives studied thus far. This, along with the base-pairing properties of TNA, warrants close scrutiny of the system in the context of the problem of RNA's origin.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Reference61 articles.

1. A. Eschenmoser in Verh. Ges. Dtsch. Naturforsch. Aerzte 11b 135 (1990); Science 284 2118 (1999).

2. The symbol (6′→4′) indicates the phosphodiester bridges of hexopyranosyl-(6′→4′) oligonucleotides connecting the C-6′ and C-4′ carbon centers of neighboring sugar units and corresponding to the (5′→3′)-connection in RNA. The symbols (4′→2′) (4′→3′) and (3′→2′) used in this paper are to be interpreted correspondingly. They also indicate in what direction the formulas of base sequences are written.

3. R. W. Fischer thesis ETH Zürich (1992)

4. A. G. Helg thesis ETH Zürich (1994)

5. K. Groebke thesis ETH Zürich (1993)

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