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

ABSTRACT: 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.

SUBMITTER: Zhang W

PROVIDER: S-EPMC3241971 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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

Zhang Wen W Huang Zhen Z

Organic letters 20110324 8

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 fo ...[more]

PMID: 21434607

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