Method for Preparing New Flavin Derivatives: Synthesis of
Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts
Christelle Frier
Jean-Luc Décout
Marc Fontecave
10.1021/jo962361w.s001
https://acs.figshare.com/articles/journal_contribution/Method_for_Preparing_New_Flavin_Derivatives_Synthesis_of_Flavin_Thymine_Nucleotides_and_Flavin_Oligonucleotide_Adducts/3705468
In order to link to the 5‘-end of oligonucleotides the
flavin analogs <b>9a</b>,<b>b</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
<b>9a,b</b> with 2-cyanoethyl
<i>N</i>,<i>N</i>-diisopropylchlorophosphoramidite, the flavin phosphoramidates <b>11a,b
</b>were isolated instead of the expected
phosphoramidite derivatives <b>10a,b</b>. A very efficient
photooxidation process occurred probably during
the isolation of the products. From the prepared flavin
H-phosphonates <b>12a,b</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 <b>15</b>−<b>17</b> 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.
1997-05-30 00:00:00
flavin analogs
phosphoramidite derivatives 10
side chain
photooxidation process
method
compounds 9
flavin phosphoramidates 11
terminal hydroxy group
methyl phosphate linkage
oxidation step
flavin analogs 9
Flavin