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  • Title: Synthesis of 5-formyl-2'-deoxyuridine and its incorporation into oligodeoxynucleotides.
    Author: Sato K, Hirose W, Matsuda A.
    Journal: Curr Protoc Nucleic Acid Chem; 2008 Dec; Chapter 1():Unit 1.21. PubMed ID: 19085981.
    Abstract:
    A straightforward, efficient method for the synthesis of 5-formyl-2'-deoxyuridine (dfU) and solid-phase synthesis of oligodeoxynucleotides containing dfU using a phosphoramidite method are described. The synthesis of dfU is achieved by oxidation of the 5-methyl group in thymidine derivatives. However, incorporation of the dfU 3'-O-phosphoramidite into oligodeoxynucleotides proceeds in low yield, due to instability of the 5-formyl group under conditions used for automated DNA synthesis. Therefore, oligodeoxynucleotides containing a 5-(1,2-dihydroxyethyl)uracil derivative are first prepared and finally oxidized by periodate to give the desired oligodeoxynucleotides containing 5-formyluracil.
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