alpha-homo-DNA and RNA form a parallel oriented non-A, non-B-type double helical structure

Autor(en): Froeyen, M
Lescrinier, E
Kerremans, L
Rosemeyer, H 
Seela, F
Verbeure, B
Lagoja, I
Rozenski, J
Van Aerschot, A
Busson, R
Herdewijn, P
Stichwörter: alpha-homo-DNA; ANOMERIC OLIGODEOXYRIBONUCLEOTIDES; ANTISENSE OLIGONUCLEOTIDES; base-pair orientation; BASE-PAIRING PROPERTIES; CHEMICAL ETIOLOGY; Chemistry; Chemistry, Multidisciplinary; CONFORMATIONAL-ANALYSIS; DNA recognition; MESSENGER-RNA; MOLECULAR-DYNAMICS; NUCLEIC-ACID STRUCTURE; oligonucleotides; P-RNA; RNA; SUGAR-PHOSPHATE BACKBONE
Erscheinungsdatum: 2001
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 7
Ausgabe: 23
Startseite: 5183
Seitenende: 5194
Zusammenfassung: 
Cross-talking between nucleic acids is a prerequisite for information transfer. The absence of observed base pairing interactions between pyranose and furanose nucleic acids has excluded considering the former type as a (potential) direct precursor of contemporary RNA and DNA. We observed that alpha -pyranose oligonucleotides (alpha -homo-DNA) are able to hybridize with RNA and that both nucleic acid strands are parallel oriented. Hybrids between alpha -homo-DNA and DNA are less stable. During the synthesis of alpha -homo-DNA we observed extensive conversion of N-6 benzoyl-5-methylcytosine into thymine under the usual deprotection conditions of oligonucleotide synthesis. alpha -Homo-DNA:RNA represents the first hybridization system between pyranose and furanose nucleic acids. The duplex formed between a-homo-DNA and RNA was investigated using CD, NMR spectroscopy, and molecular modeling. The general rule that orthogonal orientation of base pairs prevents hybridization is infringed. NMR experiments demonstrate that the base moieties of a-homo-DNA in its complex with RNA, are equatorially oriented and that the base moieties of the parallel RNA strand are pseudoaxially oriented. Modeling experiments demonstrate that the duplex formed is different from the classical A- or B-type double stranded DNA. We observed 15 base pairs in a full helical turn. The average interphosphate distance in the RNA strand is 6.2 Angstrom and in the alpha -homo-DNA strand is 6.9 Angstrom. The interstrand P-P distance is much larger than found in the typical Aand B-DNA. Most helical parameters are different from those of natural duplexes.
ISSN: 09476539
DOI: 10.1002/1521-3765(20011203)7:23<5183::AID-CHEM5183>3.0.CO;2-H

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