Supports for oligomer synthesis
View Patent ↗Universal linkers, their facile processes of manufacture and methods of using the same are provided.
1. A compound having the formula:
wherein:
one of Q 1 and Q 2 is a protecting group, a phosphodiester linked nucleoside or a phosphodiester linked oligonucleotide and the other of Q 1 and Q 2 is a linkage attached to a support medium; and
A is a substituted or unsubstituted aromatic group.
2. The compound of claim 1 wherein A is an unsubstituted aromatic group.
3. The compound of claim 1 wherein A is phenyl.
4. The compound of claim 1 wherein said linkage attached to a support medium has the formula:
—C(═O)—(CH 2 ) n —C(═O)—
wherein n is from about 2 to about 8.
5. The compound of claim 4 wherein n is 2.
6. The compound of claim 1 wherein Q 1 is a protecting group.
7. The compound of claim 1 wherein Q 2 is a protecting group.
8. The compound of claim 1 wherein one of Q 1 and Q 2 is an acid labile hydroxyl protecting group.
9. The compound of claim 8 wherein said acid labile hydroxyl protecting group is 4-methoxytriphenylmethyl, 4,4′-dimethoxytriphenylmethyl, 9-phenylxanthenyl or substituted 9-phenylxanthenyl.
10. The compound of claim 9 wherein said acid labile hydroxyl protecting group is 4,4′-dimethoxytriphenylmethyl.
11. The compound of claim 1 wherein one of Q 1 and Q 2 is a phosphodiester linked nucleoside or oligonucleotide.
12. The compound of claim 1 wherein said support medium is controlled pore glass, oxalyl-controlled pore glass, silica-containing particles, polystyrene, copolymers of polystyrene and divinylbenzene, copolymers of dimethylacrylamide and N,N-bisacryloylethylenediamine, a soluble support medium or PEPS.
13. The compound of claim 12 wherein said support medium is controlled pore glass, polystyrene or copolymers of polystyrene.
14. The compound of claim 13 wherein said support medium is controlled pore glass.
15. The compound of claim 1 wherein said support medium is HL30 Primer solid support, OligoPrep solid support, Nittomar 200 solid support or Nittomar 250 solid support.
16. The compound of claim 1 having the formula:
wherein:
one of Q 1 and Q 2 is a protecting group, a phosphodiester linked nucleoside or a phosphodiester linked oligonucleotide and the other of Q 1 and Q 2 is a linkage attached to a support medium; and
A is a substituted or unsubstituted aromatic group.
17. The compound of claim 16 having the formula:
wherein:
SM is said support material;
A is a substituted or unsubstituted aromatic group; and
Pg is an acid labile hydroxyl protecting group.
18. The compound of claim 17 wherein:
A is unsubstituted aromatic group; and
Pg is 4,4′-dimethoxytriphenylmethyl.
19. The compound of claim 18 wherein A is phenyl.
20. The compound of claim 16 having the formula:
wherein:
SM is said support material;
A is a substituted or unsubstituted aromatic group; and
Pg is an acid labile hydroxyl protecting group.
21. The compound of claim 20 wherein:
A is unsubstituted aromatic group; and
Pg is 4,4′-dimethoxytriphenylmethyl.
22. The compound of claim 21 wherein A is phenyl.
23. A racemic mixture of compounds of the formula:
wherein:
for the first percentage of the mixture Q 3 is a protecting group and Q 4 is SM-C(═O)—(CH 2 ) 2 —C(═O)— and for the second percentage of the mixture Q 3 is SM-C(═O)—(CH 2 ) 2 —C(═O)— and Q 4 is a protecting group and wherein the combined first and second percentages equal essentially 100 percent of the mixture.
24. The mixture of claim 23 wherein said protecting group is dimethoxytrityl.