Novel Reagents Utilizing A Serinol Scaffold For Labeling Synthetic Oligonucleotides
AssigneesNelson Biotechnologies, Inc., Glen Research Corporation
InventorsPaul S. Nelson, Hugh Mackie, Andrew Murphy
Life of this patent
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Abstract
Novel CE-phosphoramidites and CPG reagents have been synthesized from a serinol backbone. These reagents are useful to introduce functional groups or directly label oligonucleotides. The versatile serinol scaffold allows for labeling at any position (5′ or 3′ termini, or any internal position) during automated DNA synthesis. Multiple labels or functional groups can be achieved by repetitive coupling cycles. Optimal spacer arms and protected label moieties have been specially designed. Further, the natural 3-carbon atom internucleotide phosphate distance is retained when inserted internally.
Claims28
A reagent for use in oligonucleotide synthesis having the following structure:
- wherein:
- R1=DMT, MMT, or any other hydroxyl protecting group stable to oligonucleotide synthesis conditions.
- R2=phosphoramidite or phosphate group consisting of and salts thereof;
- wherein R3 and R4 are independently selected from the group consisting of C1-10 branched alkyl, C1-12 alkyl, and cyclic hydrocarbons;
- and R5 is any phosphate-protecting group.
- X1=spacer group that separates X2 from the 2-position serinol amino group (—NH—), X2=a functional group such as an amine, (—NH2), or sulfhydryl (—SH), or hydroxyl (—OH) which can be utilized for attaching a label or other desired molecule.
- R6=any reporter molecule including but not limited to biotin, carboxyfluorescein, propargyl, haptens, stable in oligonucleotide synthesis conditions;
- or any protecting group for the functional group X2.
Dependencies are inferred from the claim text.