Click chemistry to construct fluorescent oligonucleotides for DNA sequencing

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 609-612

  Seo, Tae Seok ^a,b   Li, Zengmin ^a,b   Ruparel, Hameer ^a,b   Ju, Jingyue ^a,b  

^a Columbia Univ Coll of Phys/Surg ^*  (United States)

^b Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; ELECTROPHORESIS; FLUORESCENCE;

DIPOLAR CYCLOADDITION;

ORGANIC COMPOUNDS;

6 CARBOXYFLUORESCEIN; AZIDE; OLIGONUCLEOTIDE; SINGLE STRANDED DNA;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DNA SEQUENCE; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOASSAY; MASS SPECTROMETRY; POLYMERASE CHAIN REACTION; PROTEIN MODIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BASE SEQUENCE; DNA; ELECTROPHORESIS, POLYACRYLAMIDE GEL; FLUORESCEINS; FLUORESCENCE; FLUORESCENT DYES; OLIGODEOXYRIBONUCLEOTIDES; SEQUENCE ANALYSIS, DNA; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0037462409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026615r     Document Type: Article

References (32)

1. Caruthers, M. H. Science 1985, 230, 281.
2. (a) Smith, L. M.; Sanders, J. Z.; Kaiser, R. J.; Hughes, P.; Dodd, C.; Connell, C. R.; Heiner, C.; Kent, S. B. H.; Hood, L. E. Nature 1986, 371, 674.
3. (b) Ju, J.; Ruan, C.; Fuller, C. W.; Glazer, A. N.; Mathies, R. A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 4347.
4. Mullis, K. B.; Faloona, F. A. Methods Enzymol. 1987, 155, 335.
5. Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99.
6. Tyagi, S.; Kramer, F. R. Nat. Biotechnol. 1996, 14, 303.
7. (a) Fodor, S. P.; Read, J. L.; Pirrung, M. C.; Stryer, L.; Lu, A. T.; Solas, D. Science 1991, 251, 767.
8. (b) Schena, M.; Shalon, D.; Davis, R. W.; Brown, P. O. Science 1995, 270, 467.
9. (a) Smith, L. M.; Fung, S.; Hunkapiller, M. W.; Hunkapiller, T. J.; Hood, L. E. Nucleic Acids Res. 1985, 13, 2399.
10. (b) Kahl, J. D.; Oreenberg, M. M. J. Am. Chem. Soc. 1999, 121, 597.
11. (c) Dey, S.; Sheppard, T. L. Org. Lett. 2001, 3, 3983.
12. Chehab, F. F.; Kan, Y. W. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9178.
13. (a) Adamczyk, M.; Chan, C. M.; Fino, J. R.; Mattingly, P. G. J. Org. Chem. 2000, 65, 596.
14. (b) Lyttle, M. H.; Walton, T. A.; Dick, D. J.; Carter, T. G.; Beckman, J. H.; Cook, R. M. Bioconjugate Chem. 2002, 13, 1146.
15. (c) Theisen, P.; McCollum, C.; Upadhya, K.; Jacobson, K.; Vu, H.; Andrus, A. Tetrahedron Lett. 1992, 33, 5033.
16. (a) Saxon, K. E.; Bertozzi, C. R. Science 2000, 287, 2007.
17. (b) Kristi, L.; Saxon, K. E.; Tirrell, D. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 19.
18. Yousaf, M. N.; Mrksich, M. J. Am. Chem. Soc. 1999, 121, 4286.
19. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2005.
20. (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053.
21. (b) Huisgen, R. Pure Appl. Chem. 1989, 61, 613,
22. (a) Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3619.
23. (b) Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Adhya, M. J. Org. Chem. 1989, 54, 5302.
24. (c) Mock, W. L. Top. Curr. Chem. 1995, 175, 1.
25. (a) Krasia, T. C.; Steinke, J. H. G. Chem. Commun. 2002, 22.
26. (b) Tuncel, D.; Steinke, J. H. G. Chem. Commun. 2002, 496.
27. (c) Tuncel, D.; Steinke, J. H. G. Chem. Commun. 2001, 253.
28. Palacios, F.; Retana, A. M.; Ragalday, J. Heterocycles 1994, 38, 95.
29. Sanger, F.; Nicklen, S.; Coulson, A. R. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 5463.
30. McGeary, R. P. Tetrahedron Lett. 1998, 39, 3319.
31. Ju, J. Anal. Biochem. 2002, 309, 35.
32. Kheterpal, I.; Mathies, R. A. Anal. Chem. 1999, 71, 31A.