Premium
Pentopyranosyl Oligonucleotide Systems. 9th Communication
Author(s) -
Pitsch Stefan,
Wendeborn Sebastian,
Krishnamurthy Ramanarayanan,
Holzner Armin,
Minton Mark,
Bolli Martin,
Miculca Christian,
Windhab Norbert,
Micura Ronald,
Stanek Michael,
Jaun Bernhard,
Eschenmoser Albert
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390349
Subject(s) - rna , oligonucleotide , chemistry , nucleic acid , computational biology , nucleic acid structure , biochemistry , dna , gene , biology
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.