5-POSITION MODIFIED PYRIMIDINES AND THEIR USE
The present disclosure relates to the field of nucleic acid chemistry, specifically to 5-position modified uridines as well as phosphoramidite and triphosphate derivatives thereof. The present disclosure also relates to methods of making and using the same.
1 . A C-5 modified aminocarbonylpyrimidine having the following structure:
wherein
R′ is selected from the group consisting of —H, —Ac, —Bz, —CH 2 CH 2 OCH 3 , —C(O)CH 2 OCH 3 and —SiMe 2 tBu;
R″ is selected from the group consisting of H, DMT and triphosphate (—P(O)(OH)—O—P(O)(OH)—O—P(O)(OH) 2 ) or a salt thereof;
X is selected from the group consisting of —H, —OH, —OMe, —O-allyl, —F, —OEt, —OPr, —OCH 2 CH 2 OCH 3 and -azido,
R is selected from the group consisting of —(CH 2 ) n —R X1 ;
R X1 is selected from the group consisting of:
R X4 is selected from the group consisting of a Cl and a nitrile (CN); and
n=0-10.
2 . A 3′-phosporamidite of a C-5 modified aminocarbonylpyrimidine having the following structure:
wherein
R″ is selected from the group consisting of H, DMT and triphosphate (—P(O)(OH)—O—P(O)(OH)—O—P(O)(OH) 2 ) or a salt thereof;
X is selected from the group consisting of —H, —OH, —OMe, —O-allyl, —F, —OEt, —OPr, —OCH 2 CH 2 OCH 3 and -azido,
R is selected from the group consisting of —(CH 2 ) n —R X1 ;
R X1 is selected from the group consisting of:
R X4 selected from the group consisting of a Cl and a nitrile (CN); and
n=0-10.
3 . A 5′-triphosphate of a C-5 modified aminocarbonylpyrimidine having the following structure:
wherein
R′ is selected from the group consisting of —H, —Ac, —Bz, —CH 2 CH 2 OCH 3 , —C(O)CH 2 OCH 3 and —SiMe 2 tBu;
X is selected from the group consisting of —H, —OH, —OMe, —O-allyl, —F, —OEt, —OPr, —OCH 2 CH 2 OCH 3 and -azido,
R is selected from the group consisting of —(CH 2 ) n —R X1 ;
R X1 is selected from the group consisting of:
R X4 selected from the group consisting of a Cl and a nitrile (CN); and
n=0-10.