%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 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.
%I ACS Publications