Nucleoside analogs with polycyclic aromatic groups attached, met

Details Nucleoside analogs with polycyclic aromatic groups attached, met Nucleoside analogs with polycyclic aromatic groups attached, met

1999-09-17

2000-10-31

Wilson, James O.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 41, C07H 1524

Patent

active

061404802

ABSTRACT:
The present invention provides fluorescent nucleosides carrying polycyclic aromatic hydrocarbons such as anthracene, phenanthrene, pyrene stilbene, tetracene or pentacene. The subject nucleosides may be synthesized using a C-glycosidic bond formation method employing organocadium or organozinc derivatives of the aromatic compounds and coupling with a 1-.alpha.-chlororibose or deoxyribose synthon. The .alpha.-anomers of the coupling reaction may be epimerized to the .beta.-anomers by acid-catalyzed equilibration. The fluorescent nucleosides act as DNA or RNA base analogs and can be incorporated into nucleic acids. Resultant fluorescently tagged nucleic acids are useful as probes for target nucleic acids in tissues, solutions or immobilized on membranes.

REFERENCES:
Bischofberger, et al., "Synthesis of Novel Polycyclic Nucleoside Analogues, Incorporation into Oligodeoxynucleotides, and Interaction with Complementary Sequences", J. Am. Chem. Soc., vol. 111:3041-3046 (1989).
Kool, et al. "Naphthalene, Phenanthrene, and Pyrene as DNA Base Analogues: Synthesis, Structure, and Fluorescene in DNA", J. Am Chem. Soc.: vol. 118: 7671-7678 (1996).
Kool, et al. "Experimental Measurement of Aromatic Stacking Affinities in the Context of Duplex DNA", J.Am. Chem. Soc.: vol. 118: 8182-8183 (1996).

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