L-α-lyxopyranosyl (4′→3′) oligonucleotides: A base-pairing system containing a shortened backbone

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1531-1534

  Reck, Folkert ^a   Wippo, Harald ^a   Kudick, René ^a   Bolli, Martin ^a   Ceulemans, Griet ^a   Krishnamurthy, Ramanarayanan ^a   Eschenmoser, Albert ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE;

ARTICLE; BASE PAIRING; CHEMISTRY; CONFORMATION; TEMPERATURE;

BASE PAIRING; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES; TEMPERATURE;

EID: 0033581786     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990184q     Document Type: Article

References (27)

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5. For recent reviews of anti-sense oligonucleotide research see e.g., Hunziker, J.; Leumann, C. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, Switzerland, 1995; Vol. 7, p 331. Hyrup, B.; Nielsen, P. E. Bioorg. Chem. Med. Chem. Lett. 1996, 4, 5. Herdewijn, P. Liebigs Ann. Chem. 1996, 1337. For exceptions from the "six-bonds rule" among oligoamide nucleic acid analogues see e.g.: Diederichsen, U.; Schmitt, H. W. Eur. J. Org. Chem. 1998, 827, 7. Diederichsen, U. Angew. Chem., Int. Ed. Engl. 1997, 36, 1886.
6. For recent reviews of anti-sense oligonucleotide research see e.g., Hunziker, J.; Leumann, C. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, Switzerland, 1995; Vol. 7, p 331. Hyrup, B.; Nielsen, P. E. Bioorg. Chem. Med. Chem. Lett. 1996, 4, 5. Herdewijn, P. Liebigs Ann. Chem. 1996, 1337. For exceptions from the "six-bonds rule" among oligoamide nucleic acid analogues see e.g.: Diederichsen, U.; Schmitt, H. W. Eur. J. Org. Chem. 1998, 827, 7. Diederichsen, U. Angew. Chem., Int. Ed. Engl. 1997, 36, 1886.
7. For recent reviews of anti-sense oligonucleotide research see e.g., Hunziker, J.; Leumann, C. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, Switzerland, 1995; Vol. 7, p 331. Hyrup, B.; Nielsen, P. E. Bioorg. Chem. Med. Chem. Lett. 1996, 4, 5. Herdewijn, P. Liebigs Ann. Chem. 1996, 1337. For exceptions from the "six-bonds rule" among oligoamide nucleic acid analogues see e.g.: Diederichsen, U.; Schmitt, H. W. Eur. J. Org. Chem. 1998, 827, 7. Diederichsen, U. Angew. Chem., Int. Ed. Engl. 1997, 36, 1886.
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20. 8 In the 2c,d series, the corresponding 3′-acetyl (instead of 3′-benzoyl) derivatives were hydrolyzed. For full experimental details on the preparation and characterization of oligonucleotide sequences in the D-β-ribopyranosyl (4′→3′) and L-α-lyxopyranosyl (4′→3′) series see a forthcoming paper by: Wippo, H.; Reck, F.; Kudick, R.; Bolli, M.; Ramaseshan, M.; Ceulemans, G.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta, in preparation.
21. Pieles, U.; Zürcher, W.; Schär, M.; Moser, H. E. Nucleic Acids Res. 1993, 21, 3191.
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23. n (n = 8, 12) may well occur in the Hoogsteen or reverse-Hoogsteen mode as opposed to duplexes containing G and C bases, in which pairing is presumably in the Watson-Crick mode. A determination would require the preparation of these duplexes in quantities sufficient for NMR analysis. For the properties of a nucleic acid analogue that pairs in the Hoogsteen mode see: Bolli, M.; Litten, J. C.; Schütz, R.; Leumann, C. J. Chem. Biol. 1996, 3, 197.
24. Micura, R.; Kudick, R.; Pitsch, S.; Eschenmoser, A. Angew. Chem., Int. Ed. 1999, 38, 680. A paper that will give a definition of the term "backbone inclination" in terms of an algorithm for the derivation of numerical values from X-ray structure data of oligonucleotide duplexes is in preparation together with M. Egli (Northwestern University).
25. In the B-type conformation of double-stranded DNA the (local) backbone axis is approximately orthogonal to the (local) base-pair axis.
26. 12
27. Marky, L. A.; Breslauer, R. J. Biopolymers 1987, 26, 1601.