Facile synthesis of a fluorescent deoxycytidine analogue suitable for probing the RecA nucleoprotein filament

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3919-3922

  Singleton, Scott F ^a   Shan, Feng ^a   Kanan, Matthew W ^a   McIntosh, Catherine M ^a   Stearman, Chad J ^a   Helm, Jeremiah S ^a   Webb, Kristofor J ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYCYTIDINE; DRUG DERIVATIVE; FLUORESCENT DYE; RECA PROTEIN;

ARTICLE; CHEMISTRY; MOLECULAR PROBE; SYNTHESIS;

DEOXYCYTIDINE; FLUORESCENT DYES; MOLECULAR PROBES; REC A PROTEIN; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0035969613     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0167863     Document Type: Article

References (29)

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11. 2AP is characterized by a relatively low emission quantum yield and excitation and emission spectra that substantially overlap those of RecA. These limitations are exacerbated by the fact that RecA protein also causes a significant background problem from light scattering.
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16. εA-Labeled DNA shows the following trend in emission intensities: free DNA < RecA-DNA < RecA-ATPγS-DNA (Cazenave, C.; Toulmé, J. J.; Hélène, C. EMBO J. 1983, 2, 2247-2251).
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21. See: Myers, A. G.; Finney, N. S.; Kuo, E. Y. Tetrahedron Lett. 1989, 30, 5747-5750, and references therein.
22. Xu, Y.-Z.; Zheng, Q.; Swann, P. F. J. Org. Chem. 1992, 57, 3839-3845.
23. For examples of this "convertible nucleoside" approach, see ref 17 as well as the following: MacMillan, A. M.; Verdine, G. L. J. Org. Chem. 1990, 55, 5931-5933. Gao, H.; Fathi, R.; Gaffney, B. L.; Goswami, B.; Kung, P.-P.; Rhee, Y.; Jin, R.; Jones, R. A. J. Org. Chem. 1992, 57, 6954-6959. Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481.
24. For examples of this "convertible nucleoside" approach, see ref 17 as well as the following: MacMillan, A. M.; Verdine, G. L. J. Org. Chem. 1990, 55, 5931-5933. Gao, H.; Fathi, R.; Gaffney, B. L.; Goswami, B.; Kung, P.-P.; Rhee, Y.; Jin, R.; Jones, R. A. J. Org. Chem. 1992, 57, 6954-6959. Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481.
25. For examples of this "convertible nucleoside" approach, see ref 17 as well as the following: MacMillan, A. M.; Verdine, G. L. J. Org. Chem. 1990, 55, 5931-5933. Gao, H.; Fathi, R.; Gaffney, B. L.; Goswami, B.; Kung, P.-P.; Rhee, Y.; Jin, R.; Jones, R. A. J. Org. Chem. 1992, 57, 6954-6959. Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481.
26. The ODN sequences used here were derived from those capable of exhibiting RecA-DNA pairing activitiy in the presence of ATPγS (Podyminogin, M. A.; Meyer, R. B.; Gamper, H. B. Biochemistry 1995, 34, 13098-13108). As a control we performed a spectroscopic ATP hydrolysis assay to show that these ODNs were competent tor activitating the RecA protein (details are available in the Supporting Information).
27. Details and graphics are available in the Supporting Information.
28. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.; Plenum Publishing: New York, 1999; Chapter 10.
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