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Titolo:
alpha-homo-DNA and RNA form a parallel oriented non-A, non-B-type double helical structure
Autore:
Froeyen, M; Lescrinier, E; Kerremans, L; Rosemeyer, H; Seela, F; Verbeure, B; Lagoja, I; Rozenski, J; Van Aerschot, A; Busson, R; Herdewijn, P;
Indirizzi:
Rega Inst Med Res, Med Chem Lab, B-3000 Leuven, Belgium Rega Inst Med ResLeuven Belgium B-3000 Chem Lab, B-3000 Leuven, Belgium Univ Osnabruck, Organ Chem Lab, D-4500 Osnabruck, Germany Univ Osnabruck Osnabruck Germany D-4500 m Lab, D-4500 Osnabruck, Germany
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 23, volume: 7, anno: 2001,
pagine: 5183 - 5194
SICI:
0947-6539(200112)7:23<5183:AARFAP>2.0.ZU;2-C
Fonte:
ISI
Lingua:
ENG
Soggetto:
NUCLEIC-ACID STRUCTURE; SUGAR-PHOSPHATE BACKBONE; BASE-PAIRING PROPERTIES; CHEMICAL ETIOLOGY; ANOMERIC OLIGODEOXYRIBONUCLEOTIDES; ANTISENSE OLIGONUCLEOTIDES; CONFORMATIONAL-ANALYSIS; MOLECULAR-DYNAMICS; MESSENGER-RNA; P-RNA;
Keywords:
alpha-homo-DNA; base-pair orientation; DNA recognition; oligonucleotides; RNA;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
75
Recensione:
Indirizzi per estratti:
Indirizzo: Herdewijn, P Rega Inst Med Res, Med Chem Lab, Minderbroedersstr 10, B-3000Leuven, Belgium Rega Inst Med Res Minderbroedersstr 10 Leuven Belgium B-3000
Citazione:
M. Froeyen et al., "alpha-homo-DNA and RNA form a parallel oriented non-A, non-B-type double helical structure", CHEM-EUR J, 7(23), 2001, pp. 5183-5194

Abstract

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 betweenpyranose 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. Mosthelical parameters are different from those of natural duplexes.

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Documento generato il 19/09/20 alle ore 21:25:31