Ketone-DNA: A versatile postsynthetic DNA decoration platform

Organic Letters

Volumn 3, Issue 25, 2001, Pages 3983-3986

  Dey, Subhakar ^a   Sheppard, Terry L ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ARGINYL-GLYCYL-ASPARTIC ACID; ARGINYLGLYCYLASPARTIC ACID; DNA; KETONE; OLIGODEOXYRIBONUCLEOTIDE; OLIGOPEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; DNA DENATURATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DNA; KETONES; MOLECULAR STRUCTURE; NUCLEIC ACID DENATURATION; OLIGODEOXYRIBONUCLEOTIDES; OLIGOPEPTIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SUPPORT, NON-U.S. GOV'T;

EID: 0035856963     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016626r     Document Type: Article

References (36)

1. For a review, see: Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99-134.
2. For a recent example, see: Taton, T. A.; Mirkin, C. A.; Letsinger, R. L. Science 2000, 289, 1757-1760.
3. Prober, J. M.; Trainor, G. L.; Dam, R. J.; Hobbs, F. W.; Robertson, C. W.; Zagursky, R. J.; Cocuzza, A. J.; Jensen, M. A.; Baumeister, K. Science 1987, 238, 336-341.
4. For reviews, see: (a) Breaker, R. R. Nature Biotechnol. 1997, 15, 427-431.
5. (b) Sen, D.; Geyer, C. R. Curr. Opin. Chem. Biol. 1998, 2, 680-687.
6. (c) Jäschke, A. Curr. Opin. Struct. Biol. 2001, 11, 321-326.
7. (a) Hwang, J. -T.; Greenberg, M. M. J. Org. Chem. 2001, 66, 363-569.
8. (b) Kahl, J. D.; Greenberg, M. M. J. Am. Chem. Soc. 1999, 121, 597-604.
9. (c) Xu, Y, -Z.; Zheng, Q.; Swann, P. F. J. Org. Chem. 1992, 57, 3839-3845.
10. (d) Ferentz, A. E.; Verdine, G. L. J. Am. Chem. Soc. 1991, 113, 4000-4002.
11. Sugar ligation: Peri, F.; Cipolla, L.; La Ferla, B.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. Aldehyde groups tor DNA ligation: Trévisiol, E.; Renard, A.; Defranq, E.; Lhomme, J. Tetrahedron Lett. 1997, 38, 8687-8690. Aldehyde-containing RNA: Berthod, T.; Petillot, Y.; Guy, A.; Cadet, A.; Forest, E.; Molko, D. Nucleosides Nucleotides 1996, 15, 1287-1306.
12. Sugar ligation: Peri, F.; Cipolla, L.; La Ferla, B.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. Aldehyde groups tor DNA ligation: Trévisiol, E.; Renard, A.; Defranq, E.; Lhomme, J. Tetrahedron Lett. 1997, 38, 8687-8690. Aldehyde-containing RNA: Berthod, T.; Petillot, Y.; Guy, A.; Cadet, A.; Forest, E.; Molko, D. Nucleosides Nucleotides 1996, 15, 1287-1306.
13. Sugar ligation: Peri, F.; Cipolla, L.; La Ferla, B.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. Aldehyde groups tor DNA ligation: Trévisiol, E.; Renard, A.; Defranq, E.; Lhomme, J. Tetrahedron Lett. 1997, 38, 8687-8690. Aldehyde-containing RNA: Berthod, T.; Petillot, Y.; Guy, A.; Cadet, A.; Forest, E.; Molko, D. Nucleosides Nucleotides 1996, 15, 1287-1306.
14. Biomolecular aminooxy ligations -oligonucleotides: (a) Defrancq, E.; Lhomme, J. Bioorg. Med. Chem. Lett. 2001, 11, 931-933.
15. (b) Trévisiol, E.; Defranq, E.; Lhomme, J.; Layoun, A.; Cros, P. Eur. J. Org. Chem. 2000, 211-217.
16. (c) Salo, H.; Virta, P.; Hakala, H.; Prakash, T. P.; Kawasaki, A. M.; Manoharan, M.; Lönnberg, H. Bioconjugate Chem. 1999, 10, 815-823.
17. (a) Rose, K. J. Am. Chem. Soc. 1994, 116, 30-33.
18. (b) Shao, J.; Tam, J. P. J. Am. Chem. Soc. 1995, 117, 3893-3899.
19. (c) Lelièvre, D.; Chabane, H.; Delmas, A. Tetrahedron Lett. 1998, 39, 9675-9678.
20. (d) Marcaurelle, L. A.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 7279-7282.
21. (e) Lelièvre, D.; Buré, C.; Laot, F.; Delmas, A. Tetrahedron Lett. 2001, 42, 235-238.
22. Cornish, V. W.; Hahn, K. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 8150-8151.
23. Mahal, L. K.; Yarema, K. J.; Bertozzi, C. R. Science 1997, 276, 1125-1128.
24. Trévisiol, E.; Defrancq, E.; Lhomme, J.; Laayoun, A.; Cros, P. Tetrahedron 2000, 56, 6501-6510.
25. Ahmadian, M.; Zhang, P.; Bergstorm, D. E. Nucleic Acids Res. 1998, 26, 3127-3135.
26. Sági, J.; Nowak, R.; Zmudzka, B.; Szemzö, A.; Ötvös, L. Biochim. Biophy. Acta 1980, 606, 196-201.
27. Sakthivel, K.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1998, 37, 2872-2875.
28. Trifluoroacetamide 7 was synthesized according to the following: Cook, A. F.; Vuocolo, E.; Brakel, C. L. Nucleic Acids Res. 1988, 16, 4077-4095. We point out that elimination of the aqueous workup increased the yield of highly water-soluble 7 from 35% to 95%.
29. (a) Hobbs, F. W., Jr. J. Org. Chem. 1989, 54, 3420-3422.
30. (b) Bergstrom, D. E.; Ruth, J. L.; Warwick; P. J. Org. Chem. 1981, 46, 1432-1441.
31. Caruthers, M. H.; Barone, A. D.; Beaucage, S. L.; Dodds, D. R.; Fisher, E. F.; McBride, L. J.; Matteucci, M.; Stabinsky, Z.; Tang, J.-Y. Methods Enzymol. 1987, 154, 287-326.
32. - calcd, 5397.67; found, 5397.8. See Supporting Information for details.
33. 3-, ionic strength (adjusted with NaCl) = 150 mM, pH = 6.96 at 37°C).
34. Jencks, W. P. Catalysis in Chemistry and Enzymology; Dover: New York, 1969; pp 463-496.
35. Following ligation reactions, excess modifiers were removed from the product by filtration through a Sephadex-G10 gel cartridge.
36. - calcd, 5546.77; found, 5547.35.