%0 Journal Article %A Frier, Christelle %A Décout, Jean-Luc %A Fontecave, Marc %D 1997 %T Method for Preparing New Flavin Derivatives:  Synthesis of Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts %U https://acs.figshare.com/articles/journal_contribution/Method_for_Preparing_New_Flavin_Derivatives_Synthesis_of_Flavin_Thymine_Nucleotides_and_Flavin_Oligonucleotide_Adducts/3705468 %R 10.1021/jo962361w.s001 %2 https://acs.figshare.com/ndownloader/files/5795916 %K flavin analogs %K phosphoramidite derivatives 10 %K side chain %K photooxidation process %K method %K compounds 9 %K flavin phosphoramidates 11 %K terminal hydroxy group %K methyl phosphate linkage %K oxidation step %K flavin analogs 9 %K Flavin %X 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 1517 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. %I ACS Publications