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 fo 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; 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 — X1 ;
R X1 is selected from the group consisting of:
R X4 is; 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 is; and n=0−10.