Biotin-phenyldiazomethane conjugates as labeling reagents at phosphate in mono and polynucleotides

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 5, 2005, Pages 1453-1461

  Bourget, Cécile ^a   Trévisiol, Emmanuelle ^a   Bridon, Isabelle ^b   Kotera, Mitsuharu ^a   Lhomme, Jean ^a   Laayoun, Ali ^b  

^a CNRS   (France)

^b BIOMÉRIEUX   (France)

Author keywords

Alkylation; Biotin labeling; Diazomethane; Nucleic acids

Indexed keywords

2 (N BIOTINOYLAMINO)ACETOPHENONE; 2 (N BIOTINOYLAMINO)ACETOPHENONE HYDRAZONE; 2 (N BIOTINOYLAMINO)PHENYLMETHYLDIAZOMETHANE; 3 (N BIOTINOYLAMINO)BENZOPHENONE; 3 (N BIOTINOYLAMINO)BENZOPHENONE HYDRAZONE; 3 (N BIOTINOYLAMINO)DIPHENYLDIAZOMETHANE; 4 (N BIOTINOYLAMINO)ACETOPHENONE; 4 (N BIOTINOYLAMINO)ACETOPHENONE HYDRAZONE; 4 (N BIOTINOYLAMINO)PHENYLMETHYLDIAZOMETHANE; 4 BIOTINOYLAMINO 2 NITROPHENYLDIAZOMETHANE; BENZENE DERIVATIVE; BIOTIN; DIAZOMETHANE; PHENYLDIAZOMETHANE; PHOSPHATE; POLYNUCLEOTIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DNA DETERMINATION; DNA MICROARRAY; DRUG CONJUGATION; RNA ANALYSIS;

BIOTIN; DIAZOMETHANE; ELECTROPHORESIS, CAPILLARY; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDES; PHOSPHATES;

EID: 13444293157     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.12.046     Document Type: Article

References (28)

1. C. Wojczewski, K. Stolze, and J.W. Engels Synlett 1999 1667
2. M.J. Davies, A. Shah, and I.J. Bruce Chem. Soc. Rev. 29 2000 97
3. M.J. O'Donnell, and L.W. McLaughlin Reporter Groups for the Analysis of Nucleic Acid Structure S.M. Hecht Bioorganic Chemistry: Nucleic Acids 1996 Oxford University Press New York 216 243
4. C. Kessler Methods for Nonradioactive Labeling of Nucleic Acids L.J. Kricka Nonisotopic Probing, Blotting, and Sequencing 1995 Academic San Diego 41 109
5. G.T. Hermanson Nucleic Acid and Oligonucleotides Modification and Conjugation G.T. Hermanson Bioconjugate Techniques 1995 Academic San Diego 639 671
6. H. Ayukawa, S. Ohuchi, M. Ishikawa, and T. Hata Chem. Lett. 1995 81
7. T. Furuta, H. Torigai, T. Osawa, and M. Iwamura J. Chem. Soc., Perkin Trans. 1 1993 3139
8. J.W. Walker, G.P. Reid, J.A. McCray, and D.R. Trentham J. Am. Chem. Soc. 110 1988 7170
9. J. Engels, and R. Reidys Experientia 34 1978 14
10. J. Engels, and E.J. Schlaeger J. Med. Chem. 20 1977 907
11. Y. Mizuno, T. Endo, T. Miyaoka, and K. Ikeda J. Org. Chem. 39 1974 1250
12. T. Endo, K. Ikeda, Y. Kawamura, and Y. Mizuno J. Chem. Soc., Chem. Commun. 1973 673
13. S. Nishimura, and M. Saneyoshi Chem. Pharm. Bull. 28 1980 1695
14. E. Sato, M. Yoshikawa, and Y. Kanaoka Chem. Pharm. Bull. 38 1990 2287
15. G. Ramsay Nature Biotechnol. 16 1998 40
16. D.J. Lockhart, and E.A. Winzeler Nature 405 2000 827
17. M. Chee, R. Yang, E. Hubbell, A. Berno, X.C. Huang, D. Stern, J. Winkler, D.J. Lockhart, M.S. Morris, and S.P.A. Fodor Science 274 1996 610
18. R.J. Cho, M. Fromont-Racine, L. Wodicka, B. Feierbach, T. Stearns, P. Legrain, D.J. Lockhart, and R.W. Davis Proc. Natl. Acad. Sci. U.S.A. 95 1998 3752
19. N. Nimura, T. Kinoshita, T. Yoshida, A. Uetake, and C. Nakai Anal. Chem. 60 1988 2067
20. Kotera, M.; Dheu, M. L.; Milet, A.; Lhomme, J.; Laayoun, A. Bioorg. Med. Chem. Lett., in press. See doi:10.1016/j.bmcl.2004.11.024
21. A. Laayoun, M. Kotera, I. Sothier, E. Trevisiol, E. Bernal-Mendez, C. Bourget, L. Menou, J. Lhomme, and A. Troesch Bioconjug. Chem. 14 2003 1298
22. C. Bourget, E. Trevisiol, J. Lhomme, M. Kotera, C. Tora, E. Bernal-Mendez, and A. Laayoun Nucleosides Nucleotides Nucleic Acids 22 2003 1371
23. W. Schroeder, and L. Katz J. Org. Chem. 19 1954 718
24. F.S. Guziec Jr., C.J. Murphy, and E.R. Cullen J. Chem. Soc., Perkin Trans. 1 1985 107
25. K. Nakagawa, H. Onoue, and K. Minami Chem. Commun. 1966 730
26. H. Zollinger Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds 1995 VCH Weinheim
27. A. Troesch, H. Nguyen, C.G. Miyada, S. Desvarenne, T.R. Gingeras, P.M. Kaplan, P. Cros, and C. Mabilat J. Clin. Microbiol. 37 1999 49
28. 21