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US 12,686,698 B2Granted
Fast deprotecting n-exocyclic amino cyclic hydrocarbon protected groups for nucleoside phosphoramidites
AssigneeAgilent Technologies, Inc.
InventorsBenjamin D. Lunstad, Douglas J. Dellinger, Robert Kaiser
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Abstract
Compounds useful for forming nucleic acids having the structure of Formula I: Each of R1 or R2 is independently selected from hydrogen, a protecting group, or a phosphoramidite group. R3 is selected from H, F, O—C1-6 alkyl, O-MOE and a removable hydroxyl-protecting group. Q is a heterocyclic base. R4 is a cyclic hydrocarbon. Also disclosed are processes for forming the nucleic acids from the compounds and the nucleic acid products produced.
Claims18
A compound having the structure of Formula I:
- wherein each of R1 or R2 is independently selected from the group consisting of a protecting group and a phosphoramidite group, provided R1 and R2 are not both protecting groups;
- wherein R3 is H, F, O—C1-6 alkyl, O-MOE, or O-thiocarbon protecting group;
- wherein Q is a heterocyclic base;
- and
- wherein R4 is cyclopentyl or cyclohexyl.
2 more elements
A method comprising:
- contacting a nucleoside residue comprising a 5′ or 3′ unprotected hydroxyl with a protected nucleotide monomer having the structure of Formula I:
- wherein each of R1 or R2 is independently selected from the group consisting of a protecting group and a phosphoramidite group, provided R1 and R2 are not both protecting groups;
- wherein R3 is H, F, O—C1-6 alkyl, O-MOE or O-thiocarbon protecting group;
- wherein Q is a heterocyclic base;
- and
- wherein R4 is cyclopentyl or cyclohexyl,
- under conditions sufficient to covalently bond said phosphoramidite group of said protected nucleotide monomer to said unprotected hydroxyl group of said nucleoside residue and produce an internucleotide bond.
4 more elements
A protected nucleic acid comprising the structure of Formula VIII:
- wherein R3 is H, F, O—C1-6 alkyl, O-MOE, or O-thiocarbon protecting group;
- wherein Q is a heterocyclic base;
- wherein R4 is cyclopentyl or cyclohexyl;
- wherein R5 is selected from the group consisting of hydrogen, a hydrocarbyl, a substituted hydrocarbyl, an aryl, and a substituted aryl;
- and
- wherein m is an integer of at least 1.
3 more elements
Dependencies are inferred from the claim text.