Purification of oligomers

Details Purification of oligomers Purification of oligomers

2005-07-26

2005-07-26

Riley, Jezia (Department: 1637)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C435S006120, C423S342000

Reexamination Certificate

active

06921818

ABSTRACT:
Compositions and methods are disclosed which facilitate purification of oligomers and other compounds. The disclosed compositions are silyl compositions that can be directly coupled, or coupled through a linking group, to a compound of interest, preferably to an oligomer at the end of oligomer synthesis. The silicon atom includes between one and three sidechains that function as capture tags. In one embodiment, the capture tags are lipophilic, which allows a derivatized oligomer to be separated from failure sequences by reverse phase chromatography. In another embodiment, the capture tags are compounds with a known affinity for other compounds, which other compounds are preferably associated with a solid support to allow chromatographic separation. Examples include haptens, antibodies, and ligands. Biotin, which can bind to or interact with a streptavidin-bound solid support, is a preferred capture tag of this type.

REFERENCES:
patent: 5113005 (1992-05-01), Celebuski
patent: 5482836 (1996-01-01), Cantor et al.
patent: 6410225 (2002-06-01), Sproat
patent: 0 571 087 (1993-11-01), None
patent: WO 97/18312 (1997-05-01), None
Benseler, et al., “Hammerhead-like Molecules Containing Non-Nucleoside Linkers Are Active RNA Catalysts”J. Am. Chem. Soc.115:8483-8484 (1993).
Cunningham, et al., “Preparative-scale purification of RNA using an efficient method which combines gel electrophoresis and column chromatography”Nuclei Acids Research24:3647-3648 (1996).
Desjardins, et al., “Pharmacokinetics of a Synthetic, Chemically Modified Hammerhead Ribozyme Against the Rat Cytochrome P-450 3A2 mRNA After Single Intravenous Injections”J. Pharmacol. Exp. Ther.278:1419-1427 (1966).
Fu, et al., “Hammerhead Ribozymes Containing Non-Nucleoside Linkers Are Active RNA Catalysts”J. Am. Chem. Soc.116:4591-4598 (1994).
Gildea, et al., “A Versatile Acid-Labile Linker for Modification of Synthetic Biomolecules”Tetrahedron Letters31:7095-7098 (1990).
Gortz & Seliger, “New Hydrophobic Protecting groups for the chemical synthesis of oligonucleotides”Angew. Chem., Int. Ed. Engl.20:681 (1981).
Green, et al., “HPLC Purification of Synthetic Oligodeoxyribo-nucleotides Containing Base- and Backbone- Modified Sequences”BioTechniques19:836-841 (1995).
Guo, et al., “Direct fluorescence analysis of genetic polymorphisms by hybridization with oligonucleotide arrays on glass supports”,Nucleic Acids Res.22:5456-5465 (1994).
Gupta, et al., “Use of the 4-methoxy-4′-octyloxytrityl group as an affinity handle for the purification of synthetic oligonucleotides”J. Chromatogr.541:341-348 (1991).
Hertel, et al., “Numbering System for the Hammerhead”Nucleic Acids Research20:3252 (1992).
Johnstone & Thorpe,Immunochemistry In Practice(Blackwell Scientific Publications, Oxford, England, 1987) pp. 209-216, 241-242, and 30-85.
Kerkhof et al., “A Comparison of Substrates for Quantifying the Signal from a Nonradiolabeled DNA Probe”Anal. Biochem.205:359-364 (1992).
Langer ,et al., “Enzymatic Synthesis of Biotin-Labeled Polynucleotides: Novel Nucleic Acid Affinity Probes”Proc. Natl. Acad. Sci. USA78:6633 (1981).
Letsinger & Wu, “Use of a Stilbenedicarboxamide Bridge in Stabilizing, Monitoring, and Photochemically Altering Folded Conformations of Oligonucleotides”J. Am. Chem. Soc.117:7323-7328 (1995).
Lyngstadaas, et al., “A synthetic, chemically modified ribozyme eliminates amelogenin, the major translation product in developing mouse enamel in vivo”EMBO Journal14:5224-5229 (1995).
Mullah & Andrus, “Purification of 5′-O-Trityl-On Oligoribonucleotides. Investigation of Phosphate Migration during Purification and Detritylation”Nucleosides&Nucleotides15:419-430 (1996).
Murray, et al., “A General Purification Procedure for Chemically Synthesized Oligoribonucleotides”Analytical Biochemistry218:177-184 (1994).
Natt, et al., “Lipocap: a Lipophillic Phosphoramidite-based Capping Reagent”Tetrahedron53(28): 9629-9636 (1997).
Olejnik, et al., “Photocleavable biotin phosphoramidite for 5′-end-labelling, affinity purification and phosphorylation of synthetic oligonucleotides”Nucleic Acids Research24:361-366 (1996).
Ortigo, et al., “Antisense Effect of Oligodeoxynucleotides with Inverted Terminal Internucleotidic Linkages: A Minimal Modification Protecting against Nucleolytic Degradation”Antisense Res. Dev.129-146 (1992).
Pannecoucke, et al., “Phosphodiester of 3 β (7 β-hydroxycholestreol) and of 5′(3′deoxy, 3′ azido-thymidine)”Tetrahedron50(4):1173-1178 (1994).
Pease, et al., “Light-generated oligonucleotide arrays for rapid DNA sequence analysis”Proc. Natl. Acad. Sci. USA91(11):5022-5026 (1994).
Polushin, et al., “On the rapid deprotection of synthetic oligonucleotides and analogs”Nucleic Acids Research22:639-645 (1995)Protein immobilization: fundamentals and applications, Richard F. Taylor, ed. (M. Dekker, New York, 1991).
Ramage & Wahl, “4-(17-Tetrabenzo[a,c,g,i]fluorenylmethyl)-4′,4′-Dimethoxytrityl Chloride: A Hydrophobic 5′-Protecting Group for the Separation of Synthetic Oligonucleotides”Tetrahedron Letters34:7133-7136 (1993).
Reddy, et al., “Methylamine Deprotection Provides Increased Yield of Oligoribonucleotides”Tetrahedron Letters36:8929-8932 (1995).
Seliger & Schmidt, “Polymer Support Synthesis. XII*. Derivatization with the 4-Decyloxytrityl Group as an Aid in the Affinity Chromatography of Oligo- and Polynucleotides”J. Chromatogr.397:141-151 (1987).
Seliger, et al., “Solid-Phase Oligonucleotides Synthesis with Affinity-Chromatographic Separation of the Product”Tetrahedron Letters24:2115-2118 (1978).
Sinha, et al., “Polymer support oligonucleotide synthesis XVIII1.2): use of β-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product”Nucleic Acids Research12:4539-4557 (1984).
Sproat, et al., “An Efficient Method for the Isolation and Purification of Oligoribonucleotides”Nucleosides&Nucleotides14:255-273 (1995).
Stimpson, et al., “Real-time detection of DNA hybridization and melting on oligonucleotide arrays by using optical wave guides”Proc. Natl. Acad. Sci. USA92:6379-6383 (1995).
Swiderski, et al., “Polystyrene Reverse-Phase Ion-Pair Chromatography of Chimeric Ribozymes”Analytical Biochemistry216:83-88 (1994).
Syvänen, et al., “Fast quantification of nucleic acid hybrids by affinity-based hybrid collection”Nucleic Acids Res.14:5037 (1986).
Tsurui, et al., “Batchwise Purification of Specific tRNAs by a Solid-Phase DNA Probe”Analytical Biochemistry221:166-172 (1994).
Usman, et al., “Automated Chemical Synthesis of Long Oligoribonucleotides Using 2′-O-Silylated Ribonucleoside 3′-O-Phosphoramidites on a Controlled-Pore Glass Support: Synthesis of a 43-Nucleotide Sequence Similar to the 3′-Half Molecule of anEscherichia coliFormylmethionine tRNA”J. Am. Chem. Soc.109:7845-7854 (1987).
Wincott, et al., “Synthesis, deprotection, analysis and purification of RNA and ribozymes”Nucleic Acids Research23:2677-2684 (1995).

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