Click nucleic acids
Click nucleic acid monomers and polymers containing such monomers are disclosed. The click nucleic acid monomers include an optionally protected thiol moiety, an optionally protected thiol-click acceptor moiety, and an optionally protected nucleobase (NB), which in some examples is an A, G, T, U, or C nucleobase. In some examples, the click nucleic acid monomer includes a N-vinyl thiol acetamide (VTA) backbone. In other examples the click nucleic acid monomer includes a N-vinyl thiol ethylamine (VTE) backbone. Methods of using such polymers, for example in place of naturally occurring nucleic acid polymer applications, such as DNA or RNA, and synthetic nucleic acid polymer applications, such as PNA or morpholino nucleic acids, are also disclosed.
1. A click nucleic acid monomer, having the formula:
wherein T is an optionally protected thiol;
TCA is a thiol-click acceptor having the formula:
—CH═CH 2 ;
NS has the formula:
NB is an optionally protected nucleobase.
2. The click nucleic acid monomer of claim 1 , wherein the monomer comprises, an A, G, T, U, or C nucleobase having the formula:
3. The click nucleic acid monomer of claim 1 , wherein the thiol has the formula:
wherein p is an integer from 0 to 4.
4. A click nucleic acid monomer having the formula:
wherein NB is a nucleobase.
5. The click nucleic acid monomer according to claim 4 , wherein the nucleobase has the formula:
6. A click nucleic acid monomer having the formula:
wherein:
NB is a nucleobase;
T is an optionally protected thiol;
R 5 , R 6 and R 7 are each independently chosen from hydrogen or alkyl.
7. The click nucleic acid according to claim 6 , wherein T is a thiol having the formula:
8. The click nucleic acid according to claim 6 , wherein T is a protected thiol having the formula:
9. The click nucleic acid according to claim 8 , wherein protecting group is chosen from methoxytrityl, acetamidomethyl or nitrobenzyl.
10. The click nucleic acid according to claim 6 , having the formula:
11. The click nucleic acid monomer according to claim 6 , wherein the nucleobase has the formula: