Compounds for protecting hydroxyls and methods for their use
View Patent ↗A hydrocarbyldithiomethyl-modified compound of the Formula: R 1 —O—CH 2 —S—S—R 2 or a salt thereof wherein R 1 is an organic molecule and R 2 is a hydrocarbyl is useful for protecting and/or blocking hydroxyl groups in organic molecules such as nucleotides. The hydrocarbyldithiomethyl-modified compounds can also be used for chemically synthesizing oligonucleotides and for sequencing nucleic acid compounds.
1. A hydrocarbyldithiomethyl-modified compound comprising the formula:
or a salt thereof, wherein
R 1 is H, a protecting group, phosphate, diphosphate, triphosphate, or residue of a nucleic acid;
R 2 is a nucleobase;
R 3 is H, OH, or a protected form of OH; and
R 4 , R 5 and R 6 are together or separately H, hydrocarbyl, or a residue of a solid support.
2. The compound of claim 1 wherein R 4 , R 5 and R 6 together or separately further comprise a labeling group.
3. The compound of claim 1 wherein R 4 , R 5 and R 6 comprise together or separately an electron donating or withdrawing function.
4. The compound of claim 3 wherein said electron donating or withdrawing function contains a heteroatom selected from the group consisting of oxygen, nitrogen, sulfur, and silicon.
5. The compound of claim 1 wherein R 4 , R 5 and R 6 are together or separately H, methyl, ethyl, isopropyl, t-butyl, phenyl, or benzyl and wherein either R 4 , R 5 and R 6 is modified with a labeling group.
6. A compound comprising the Formula:
or a salt thereof, wherein
R 1 is H, a protecting group, a phosphate, diphosphate, or a triphosphate, or a residue of a nucleic acid;
R 2 is a nucleobase;
R 3 is H or OH, or a protected form of OH; and
R 4 is H or hydrocarbyl.
7. The compound of claim 6 wherein R 4 is modified with a labeling group.
8. The compound of claim 6 wherein R 4 comprises nitrogen.
9. The compound of claim 6 wherein R 4 is covalently linked to a solid support.