Reagents for the improved synthesis of isoguanosine containing oligonucleotides
View Patent ↗The present invention provides the combination of the O-2 diphenylcarbamoyl (“DPC”) and N-6 dimethylaminomethylidene (“DMF”) protecting groups for isoguanosine nucleosides that can be utilized in oligonucleotide synthesis.
1. A compound of the formula:
2. A compound of the formula:
wherein
E is an acid labile protecting group;
A is an O-phosphoramidite protecting group orthogonal to E;
D is NT 1 T 2 wherein
T 1 and T 2 are each, independently, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted aralkyl group; or
T 1 and T 2 taken together with the nitrogen to which they are bonded form a heterocycloalkyl group or a herteroaromatic group; and
G 1 and G 2 are substituted or unsubstituted hydrocarbon radicals.
3. The compound of claim 2 wherein E is a substituted trityl or pixyl.
4. The compound of claim 2 wherein A is, independently, cyanoethyl, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aromatic group.
5. The compound of claim 2 wherein G 1 and G 2 are each a phenyl group.
6. The compound of claim 2 wherein E is 4′,4-dimethoxytrityl.
7. The compound of claim 2 wherein A is cyanoethyl.
8. The compound of claim 2 wherein T 1 and T 2 is an isopropyl group.
9. The compound of claim 2 wherein T 1 and T 2 are each independently a substituted or unsubstituted aliphatic group.
10. The compound of claim 9 wherein T 1 and T 2 are each independently a lower alkyl group.
11. The compound of claim 2 wherein G 1 and G 2 are each independently a substituted or unsubstituted aliphatic or aromatic monovalent, or, when taken together, divalent radical, having from one to 20 carbon atoms.
12. The compound of claim 11 wherein G 1 and G 2 are each a substituted or unsubstituted aromatic group.