189748-91-2Relevant academic research and scientific papers
Method for preparing new flavin derivatives: Synthesis of flavin-thymine nucleotides and flavin-oligonucleotide adducts
Frier, Christelle,Decout, Jean-Luc,Fontecave, Marc
, p. 3520 - 3528 (2007/10/03)
In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.
