Reversible modifications of nucleotides
Disclosed herein, inter alia, are methods for modifying a nucleotide, for example including reacting a nucleotide having a 3′-O-oxime moiety such as with a reagent having an —ONH 2 moiety to produce a nucleotide having a 3′-O—NH 2 moiety such as wherein the reagent having the —ONH 2 moiety further comprises alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, heteroalicyclyl, aralkyl, heteroaralkyl, or (heteroalicyclyl)alkyl.
1. A method for modifying a nucleotide, comprising reacting a nucleotide comprising a 3′-O-oxime moiety with a reagent to produce a nucleotide comprising a 3′-O—NH 2 moiety,
wherein the nucleotide that comprises the 3′-O-oxime moiety is:
wherein the nucleotide that comprises the 3′-O—NH 2 moiety is:
wherein B is a nucleobase; R1 is halogen, OCH 3 , H or OH, Q is monophosphate, diphosphate, or triphosphate, and R3 and R4 are H, CH 3 , alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, heteroalicyclyl, aralkyl, heteroaralkyl, (heteroalicyclyl)alkyl, wherein either R3 or R4, or both R3 and R4 are not H; and,
wherein the reagent is independently:
2. The method of claim 1 , wherein R3 is —CH 3 .
3. The method of claim 1 , wherein R4 is —CH 3 .
4. The method of claim 1 , wherein Q is triphosphate.
5. The method of claim 1 , wherein the reagent is
6. The method of claim 1 , wherein the reagent is