Pentopyranosyl Oligonucleotide Systems. 9th Communication

The β-D-Ribopyranosyl-(4′→2′)-oligonucleotide System (‘Pyranosyl-RNA’): Synthesis and Resumé of Base-Pairing Properties

Authors

  • Stefan Pitsch,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH September 1992 – February 1995;

  • Sebastian Wendeborn,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH November 1992 – December 1993;

  • Ramanarayanan Krishnamurthy,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH July 1992 – December 1994 and TSRI 1996 –;

  • Armin Holzner,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH April 1992 – October 1993;

  • Mark Minton,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH September 1993 – April 1994;

  • Martin Bolli,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH and TSRI January 1995 – June 1997;

  • Christian Miculca,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: Universität Frankfurt October 1993 – März 1995;

  • Norbert Windhab,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: Universität Frankfurt 1993 – 1995;

  • Ronald Micura,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: ETH and TSRI January 1996 – June 1998;

  • Michael Stanek,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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    • Postdoctorate: TSRIJune 1998 – June 1999.

  • Bernhard Jaun,

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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  • Albert Eschenmoser

    1. Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Hönggerberg, HCI H309, CH-8093 Zürich and The Skaggs Institute for Chemical Biology at The Scripps Research Institute(TSRI), 10550 North Torrey Pines Road, La Jolla, CA-92037, USA
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  • For communications No. 1–8 see [1–8]. The label ‘Chemistry of Pyranosyl-RNA’ previously used for the series of papers on p-RNA [1–8] has been changed (see [9]) into ‘Pentopyranosyl Oligonucleotide Systems’ as a consequence of the extension of our work on p-RNA to a whole family of diastereoisomeric pentopyranosyl oligonucleotides. In [9], the present paper had been assigned No. 9 in this series. The follow-up papers No. 10 [9], 11 [10], 12 [11], and 13 [12] in the series have already appeared. The present paper also is communication No. 30 in the series ‘Chemistry ofα-Aminonitriles’. The assignment of papers in this latter series is as follows: No. 29 is [13], [14] counts as No. 28, [15] is No. 27, [16] is No. 26, [17] counts as No. 25, [8] is No. 24, [7] counts as No. 23, [18] is No. 22, [5] No. 21, [6] No. 20, [4] counts as No. 19, [3] is No. 18, [19] No. 17, [2] No. 16, [20] No. 15, [21] No. 14, [22] No. 13, [23] No. 12, and [1] is No. 11; the communication assigned to be No. 10 [24] has not appeared yet; [25] is No. 9, [26] No. 8, [27] No. 7, [28] No. 6, [29] No. 5, [30] No. 4, [31] No. 3, [32] No. 2, and [33] is No. 1.

Abstract

Pyranosyl-RNA (‘p-RNA’ ) is an oligonucleotide system isomeric to natural RNA and composed of the very same building blocks as RNA. Its generational, chemical, and informational properties are deemed to be those of an alternative nucleic acid system that could have been a candidate in Nature's evolutionary choice of the molecular basis of genetic function. We consider the study of the chemistry of p-RNA as etiologically relevant in the sense that knowledge of its structural, chemical, and informational properties on the chemical level offers both a perspective and reference points for the recognition of specific structural assets of the RNA structure that made it the (supposedly) superior system among possible alternatives and, therefore, the system that became part of biology as we know it today. The paper describes the chemical synthesis of β-d- (and L)-ribopyranosyl-(4′→2′)-oligonucleotide sequences, presents a resume of their structural and chemical properties, and cautiously discusses what we may and may not have learned from the pyranosyl isomer of RNA with respect to the conundrum of RNA's origin.

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