Design of a new fluorescent cofactor for DNA methyltransferases and sequence-specific labeling of DNA

Journal of the American Chemical Society

Volumn 125, Issue 12, 2003, Pages 3486-3492

  Pljevaljcic, Goran ^a   Pignot, Marc ^a,b   Weinhold, Elmar ^a,c  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b Nanogen Recognomics GmbH   (Germany)

^c RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDES;

CATALYSIS; ENZYMES; FLUORESCENCE; MASS SPECTROMETRY; SUBSTITUTION REACTIONS;

DNA SEQUENCES;

ADENINE; ADENOSINE DERIVATIVE; AZIRIDINE DERIVATIVE; CYTOSINE; DNA; DNA METHYLTRANSFERASE; OLIGODEOXYNUCLEOTIDE; PLASMID DNA;

ARTICLE; CATALYSIS; DNA METHYLATION; ENZYME ACTIVITY; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; SYNTHESIS; THERMUS AQUATICUS;

AZIRIDINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; FLUORESCENT DYES; MODELS, MOLECULAR; OLIGONUCLEOTIDES; PLASMIDS; SITE-SPECIFIC DNA-METHYLTRANSFERASE (ADENINE-SPECIFIC); SUBSTRATE SPECIFICITY;

EID: 0242500918     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021106s     Document Type: Article

References (30)

1. The following abbreviations are used: PCR, polymerase chain reaction; MTase, methyltransferase; AdoMet, S-adenosyl-L-methionine; M′TaqI, DNA methyltransferase from Thermus aquaticus; EDIA. N-ethyldiisopropylamine; M′HhaI, DNA methyltransferase from Haemophilus haemolyticus; M·PvuII, DNA methyltransferase from Proteus vulgaris; DpnM, DNA methyltransferase from Streptococcus pneumoniae; M·RsrI, DNA methyltransferase from Rhodopseudomonas sphaeroides; M·MboII, DNA methyltransferase from Moraxella bovis; ESI-MS, electrospray ionization mass spectrum/spectrometry; TLC, thin-layer chromatography.
2. Thuong, N. T.; Hélène, C. Angew. Chem. 1993, 105, 697-723; Angew. Chem., Int. Ed. Engl. 1993, 32, 666-690.
3. Thuong, N. T.; Hélène, C. Angew. Chem. 1993, 105, 697-723; Angew. Chem., Int. Ed. Engl. 1993, 32, 666-690.
4. Wittung, P.; Nielsen, P. E.; Buchhardt, O.; Egholm, M.; Nordén, B. Nature 1994, 368, 561-563.
5. White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Nature 1998, 391, 468-471.
6. Jamieson, A. C.; Kim, S.-H.; Wells, J. A. Biochemistry 1994, 33, 5689-5695. Rebar, E. J.; Pabo, C. O. Science 1994, 263, 671-673. Wu, H.; Yang, W.-P.; Barbas, C. F., III. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 344-348. Greisman, H. A.; Pabo, C. O. Science 1997, 275, 657-661.
7. Jamieson, A. C.; Kim, S.-H.; Wells, J. A. Biochemistry 1994, 33, 5689-5695. Rebar, E. J.; Pabo, C. O. Science 1994, 263, 671-673. Wu, H.; Yang, W.-P.; Barbas, C. F., III. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 344-348. Greisman, H. A.; Pabo, C. O. Science 1997, 275, 657-661.
8. Jamieson, A. C.; Kim, S.-H.; Wells, J. A. Biochemistry 1994, 33, 5689-5695. Rebar, E. J.; Pabo, C. O. Science 1994, 263, 671-673. Wu, H.; Yang, W.-P.; Barbas, C. F., III. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 344-348. Greisman, H. A.; Pabo, C. O. Science 1997, 275, 657-661.
9. Jamieson, A. C.; Kim, S.-H.; Wells, J. A. Biochemistry 1994, 33, 5689-5695. Rebar, E. J.; Pabo, C. O. Science 1994, 263, 671-673. Wu, H.; Yang, W.-P.; Barbas, C. F., III. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 344-348. Greisman, H. A.; Pabo, C. O. Science 1997, 275, 657-661.
10. Kessler, C. In Nonisotopic Probing, Blotting, and Sequencing; Kricka, L. J., Ed.; Academic Press: San Diego, 1995; pp 41-109.
11. Cheng, X. Annu. Rev. Biophys. Biomol. Struct. 1995, 24, 293-318.
12. Pignot, M.; Siethoff, C.; Linscheid, M.; Weinhold, E. Angew. Chem. 1998, 110, 3050-3053; Angew. Chem., Int. Ed. 1998, 37, 2888-2891.
13. Pignot, M.; Siethoff, C.; Linscheid, M.; Weinhold, E. Angew. Chem. 1998, 110, 3050-3053; Angew. Chem., Int. Ed. 1998, 37, 2888-2891.
14. Pignot, M.; Pljevaljcic, G.; Weinhold, E. Eur. J. Org. Chem. 2000, 549-555.
15. Labahn, J.; Granzin, J.; Schluckebier, G.; Robinson, D. P.; Jack, W. E.; Schildkraut, I.; Saenger, W. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 10957-10961.
16. Schluckebier, G.; Kozak, M.; Bleimling, N.; Weinhold, E.; Saenger, W. J. Biol. Chem. 1997, 265, 56-67.
17. Goedecke, K.; Pignot, M.; Goody, R. S.; Scheidig, A. J.; Weinhold, E. Nat. Struct. Biol. 2001, 8, 121-125.
18. Ikehara, M.; Tada, H.; Kaneko, M. Tetrahedron 1968, 24, 3489-3498.
19. Reinstein, J.; Vetter, I. R.; Schlichting, I.; Rösch, P.; Witfinghofer, A.; Goody, R. S. Biochemistry 1990, 29, 7440-7450.
20. Klimasauskas, S.; Kumar, S.; Roberts, R. J.; Cheng, X. Cell 1994, 76, 357-369.
21. Gong, W.; O'Gara, M.; Blumenthal, R. M.; Cheng, X. Nucleic Acids Res. 1997, 25, 2702-2715.
22. Tran, P. H.; Korszun, Z. R.; Cerritelli, S.; Springhorn, S. S.; Lacks, S. A. Structure 1998, 6, 1563-1575.
23. Scavetta, R. D.; Thomas, C. B.; Walsh, M. A.; Szegedi, S.; Joachimiak, A.; Gumport, R. I.; Churchill, M. E. A. Nucleic Acids Res. 2000, 28, 3950-3961.
24. Osipiuk, J.; Walsh, M. A.; Joachimiak, A. Protein Data Bank, entry number 1G60.
25. Gabriel, S. Chem. Ber. 1888, 21, 2664-2669. Gabriel, S.; Stelzner, R. Chem. Ber. 1895, 8, 2929-2938.
26. Gabriel, S. Chem. Ber. 1888, 21, 2664-2669. Gabriel, S.; Stelzner, R. Chem. Ber. 1895, 8, 2929-2938.
27. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
28. Wilm, M.; Mann, M. Anal. Chem. 1996, 68, 1-8.
29. Leatherbarrow, R. J. 1992, GraFit, Version 3.0; Erithacus Software Ltd.: Staines, U.K.
30. Cantor, C. R.; Warshaw, M. M.; Shapiro, H. Biopolymers 1970, 9, 1059-1077.