- Preparation of stilbene-tethered nonnatural nucleosides for use with blue-fluorescent antibodies
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The synthesis of the first examples of stilbene-tethered hydrophobic C-nucleosides is described. Compounds of this type are targeted for use with our recently reported "blue-fluorescent antibodies with the aim of probing native and nonnatural DNA. The nucleophilic addition of aryl Grignard reagents to either a protected 2′-deoxy-1′-chloro-ribofuranose or a protected 2′-deoxy-ribonolactone was the key synthetic step and afforded C-nucleosides in good yields. Both routes resulted in a final product that was ≥ 90% of the β-anomer. Amide- and ether-based linkers for attachment of trans-stilbene to the nucleobase were assessed for utility during synthesis and in binding of the ligands to a blue-fluorescent monoclonal antibody. X-ray structures of each complex were obtained and serve as a guideline for second-generation stilbene-tethered C-nucleosides. The development of these hydrophobic nucleosides will be useful in current native and nonnatural DNA studies and invaluable for investigations regarding novel, nonnatural genomes in the future.
- Chen,Beuscher IV,Stevens,Wirsching,Lerner,Janda
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- Anti-stilbene antibodies
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The present invention provides an anti-stilbene antibody. Preferably, the antibody is a monoclonal antibody. Exemplary and preferred such antibodies are designated herein as 19G2, 20F2, 21C6, 22B9, 25F8, 25E2, 23E4, 23G3, 23D3, 23C2, 25C10, 24B6, 21E2, 16
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