Precursors for two-step polynucleotide synthesis

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S026800, C536S027600, C536S027810, C536S028500

Reexamination Certificate

active

07427679

ABSTRACT:
Precursors for use in the synthesis of polynucleotides are disclosed. The precursors include a heterocyclic base having an exocyclic amine group and a substituted or unsubstituted triaryl methyl protecting group bound to the exocyclic amine group. In particular embodiments, the precursor has the structure:wherein:O and H represent oxygen and hydrogen, respectively,R1is hydrido, hydroxyl, protected hydroxyl, lower alkyl, modified lower alkyl, or alkoxy,one of R2or R3is a hydroxyl protecting group; and the other of R2or R3is a reactive group capable of reacting with a reactive site hydroxyl,Base is a heterocyclic base having an exocyclic amine group, andTram is a triaryl methyl group having the structure (V)wherein the broken line represents a bond to the amino nitrogen of the exocyclic amine group, and R4, R5and R6are independently selected from unsubstituted or substituted aryl groups, provided that at least one of R4, R5, and R6is an aryl group other than phenyl and other than substituted phenyl.

REFERENCES:
patent: 4500707 (1985-02-01), Caruthers et al.
patent: 4668777 (1987-05-01), Caruthers et al.
patent: 6222030 (2001-04-01), Dellinger et al.
patent: 6258454 (2001-07-01), Lefkowitz et al.
patent: 6630581 (2003-10-01), Dellinger et al.
patent: 7101986 (2006-09-01), Dellinger et al.
patent: 7193077 (2007-03-01), Dellinger et al.
patent: 2002/0045221 (2002-04-01), Dellinger
patent: 2002/0058802 (2002-05-01), Dellinger et al.
patent: 2003/0129589 (2003-07-01), Koster et al.
patent: 0241363 (1987-10-01), None
patent: 1428810 (2004-06-01), None
patent: WO92/10092 (1992-06-01), None
Kochetkov et al., “Reactions of Exocyclic Substituents of Nucleic Acid Bases and their Derivatives,” Chapter 6 inOrganic Chemistry of Nucleic Acids, Part B, Kochetkov et al. (eds.), Plenum Press, New York, NY, 1972, only pp. 367-368 and 376-378 supplied.
Michelson et al., “Nucleotides. Part III. Mononucleotides derived from Adenosine, Guanosine, Cytidine and Uridine,”Journal of the Chemical Society, 1949, pp. 2476-2486.
Smith et al., “Studies on Polynucleotides. XIV. Specific Synthesis of the C3′-C5′ Internucleotide Linkage. Synthesis of Uridylyl-(3′-5′)-Uridine and Uridylyl-(3′-5′)-Adenosine,”J. Amer. Chem. Soc., 84, 430-440 (Feb. 5, 1962).
Ralph et al., “Studies on Polynucleotides. XVIII. Experiments on the Polymerization of Mononucleotides. The Synthesis and Characterization of Deoxyguanosine Oligonucleotides,”J. Amer. Chem. Soc., 85, 1983-1988 (Jul. 5, 1963).
Schaller et al., “Studies on Polynucleotides. XXIV. The Stepwise Synthesis of Specific Deoxyribopolynucleotides (4). Protected Derivatives of Deoxyribonucleosides and New Syntheses of Deoxyribonucleoside-3′ Phosphates,”J. Amer. Chem. Soc., 85, 3821-3827 (Dec. 5, 1963).
Brimacombe et al., “Oligonucleotidic Compounds. XXIII. Protected Derivatives of Guanosine and Adenosine 3′-Phosphates. A Synthesis of Diribonucleoside Phosphates Starting from Adenosine and Guanosine Derivatives Bearing a Free NH2Group,”Collection Czechoslov. Chem. Commun., 33, 2074-2086 (1968).
Kochetkov et al., “Reactions of Exocyclic Substituents of Nucleic Acid Bases and their Derivatives,” Chapter 6 in Organic Chemistry of Nucleic Acids, Part B, Kochetkov et al. (eds.), Plenum Press, New York, NY, 1972, only pp. 367-368 and 376-378 supplied.
Michelson et al., “Nucleotides. Part III. Mononucleotides derived from Adenosine, Guanosine, Cytidine and Uridine,” Journal of the Chemical Society, 1949, pp. 2476-2486.
Smith et al., “Studies on Polynucleotides. XIV. Specific Synthesis of the C3′-C5′ Internucleotide Linkage. Synthesis of Uridylyl-(3′-5′)-Uridine and Uridylyl-(3′-5′)-Adenosine,” □□ J. Amer. Chem. Soc., 84, 430-440 (Feb. 5, 1962).
Ralph et al., “Studies on Polynucleotides. XVIII. Experiments on the Polymerization of Mononucleotides. The Synthesis and Characterization of Deoxyguanosine Oligonucleotides,”□□ J. Amer. Chem. Soc., 85, 1983-1988 (Jul. 5, 1963).
Schaller et al., “Studies on Polynucleotides. XXIV. The Stepwise Synthesis of Specific Deoxyribopolynucleotides (4). Protected Derivatives of Deoxyribonucleosides and New Syntheses of Deoxyribonucleoside-3′ Phosphates,” J. Amer. Chem. Soc., 85, 3821-3827 (Dec. 5, 1963).
Brimacombe et al., “Oligonucleotidic Compounds. XXIII. Protected Derivatives of Guanosine and Adenosine 3′-Phosphate, A Synthesis of Diribonucleoside Phosphates Starting from Adenosine and Guanosine Derivatives Bearing a Free NH2 Group,” Collection Czechoslov. Chem. Commun., 33, 2074-2086 (1968).
Nyllas A., et al., “Synthesis of [3′(O)>5′(C)]Oxyacetamido linked nucleosides”, Tetrahedron, vol. 46, No. 6, 1990, pp. 2149-2164.
Sekine, et al., “Introduction of the 4, 4′,4″-Tris (Benzoyloxy)trityl group inot the exo amino groups of into the exo amino groups of deoxyribonucleotides and its properties” Tetrahedron, vol. 41, No. 23, 1985, pp. 5445-5453.
Sekine, et al., “Synthesis of Short Oligoribonucleotides bearing a 3′—or 5′—terminal phosphates by use of 4, 4″, 4″ -tris (4, 5-dichlorophtalimido)trityl) as a new 5′ -hydroxyl protecting group” J. Amer. Chem. Society vol. 108, 1986, pp. 4581-4586.
Mishra, Rakesh K. et a., “Protecting groups as purification tool in large-scale synthesis of small oligodeoxyribonucleotides”, Indian Journal of Chemistry, 1988, 27B(9), 817-20.
Sekine et al., “Synthesis of Oligodeoxyribonucleotides Involving a Rapid Procedure for Removal of Base-Protecting Groups by Use of the 4,4′, 4″- Tris(benzoyloxy) trityl (TBTr) Group”, Bull. Chem. Soc. Japan, 59, pp. 1781-1789, (1986).
Kamimura et al., “Synthesis of a Dodecaribonuecleotide, GUAUCAAUAAUG, by Use of “Fully” Protected Ribonucleotide Building Blocks”, J. Am. Chem. Soc. 1984, vol. 106 4552-4557.
Will et al., “The Synthesis of Polyamide Nucleic Acids using a Novel Monomethoxytrityl Protecting-Group Strategy”, Tetrahedron, vol. 51, No. 44, pp. 12069-12082, 1985.
Katzhendler et al., “The Effect of Spacer, Linkage and Solid Support on the Synthesis of Oligonucleotides”, Tetrahedron, vol. 45, No. 9, pp. 2777-2792, 1989.
Iwase et al, “A New Method for the Synthesis of Capped Oligoribonucleotides by Use of an Appropriately Protected 7-Methylguanosine Diphosphate Derivative as a Donor for the Triphosphate Derivative as a Donor for the Triphosphate Bond Formation”, Tetrahedron Letters, vol. 29, No. 24, pp. 2969-2972, 1988.

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