Synthesis of a novel pyrene-containing nucleoside and its incorporation into oligonucleotides

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1279-1282

  Frazer, Jennifer D ^a   Horner, Stacy M ^a   Woski, Stephen A ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE ANALOG; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRENE DERIVATIVE;

ARTICLE; SYNTHESIS;

EID: 0032510289     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10853-X     Document Type: Article

References (22)

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9. 6. Although these compounds are formally derivatives of 3-deoxy-D-allonic acid, ribofuranose nomenclature and numbering are used throughout to emphasize their relationship to natural nucleosides.
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12. 3, H-2)
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15. 3).
16. 13. Herzig, J.; Nudelman, A.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 1986, 51, 727-730.
17. 3OD): 8.26 (d, J = 8.2 Hz, 1H, pyrene), 8.21-8.17 (m, 4H, pyrene), 8.12 (d, J = 9.3 Hz, 1H, pyrene), 8.05 (s, 2H, pyrene), 8.01 (t, J = 7.6 Hz, 1H, pyrene), 4.91 (apparent t, J = 7.6 Hz, 1H, H-1′), 4.49 (ddd, J = 6.5, 4.7, 3.9 Hz, 1H, H-3′), 4.12 (ddd, J = 4.1, 3.9, 3.4 Hz, 1H, H-4′), 3.95 (dd, J = 11.9, 3.4 Hz, 1H, H-5a′), 3.81 (dd, J = 11.9, 4.1 Hz, 1H, H-5b′), 2.54-2.44 (m, 2H, H-2′).
18. 15. This product was isolated as a single diastereomer which has been assigned as the β-configuration based on the "peak width rule" of Srivastava, et al. (J. Heterocyclic Chem. 1981, 18, 1659-1662). Studies to unequivocally assign the anomeric stereochemistry are currently underway.
19. 16. Coupling yields were determined by spectrophotometric quantitation of the dimethoxytrityl cation.
20. 17. Oligonucleotide syntheses were performed on a Perkin Elmer ABI 391 DNA synthesizer on a 0.2 μmol scale using the standard protocol supplied by the manufacturer.
21. 18. Glen Research Corporation 1997 Catalog, p 31.
22. 19. Nucleoside 4 was unchanged upon treatment with 0.05 M potassium carbonate in methanol for 2 h as was determined by TLC analysis.