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Org Lett. 2011 Apr 15;13(8):2000-3. doi: 10.1021/ol200397c. Epub 2011 Mar 24.

Synthesis of the 5'-Se-thymidine phosphoramidite and convenient labeling of DNA oligonucleotide.

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  • 1Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA.


The synthesis of the 5'-Se-derivatized thymidine and phosphoramidite is reported, and the Se-phosphoramidite was incorporated into DNA. Because of its high nucleophilicity, this 5'-Se-moiety permits convenient postsynthetic modification of oligonucleotides. The proof of principle was successfully demonstrated by incorporating fluorescein into DNA. It was also found that the 5'-dye-labeled Se-DNA can be recognized by DNA polymerase as an efficient primer. This novel strategy opens a new avenue for nucleic acid probe preparation and detection.

© 2011 American Chemical Society

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