Backbone modified oligonucleotide analogs and solid phase synthe

Details Backbone modified oligonucleotide analogs and solid phase synthe Backbone modified oligonucleotide analogs and solid phase synthe

1993-12-28

1996-07-30

Robinson, Douglas W.

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

Organic compounds

Carbohydrates or derivatives

536 253, 536 2532, 536 2533, 536 2534, 536 256, C07H 100, C07H 1900, C07H 2100

Patent

active

055413072

ABSTRACT:
Compounds and methods for preparing oligonucleotide analogs are provided. In preferred embodiments, the methods involve solid-phase coupling of synthons bearing either 3'-electrophillic groups and 5'-nucleophilic groups or 5'-electrophillic groups and 3'-nucleophilic groups to form neutral, achiral oligomers.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan, Jr. et al.
patent: 4707440 (1987-11-01), Stavrianopoulos
patent: 5138045 (1992-08-01), Cook et al.
patent: 5223618 (1993-06-01), Cook et al.
patent: 5378825 (1995-01-01), Cook et al.
patent: 5386023 (1995-01-01), Sanghvi et al.
Alul et al., "Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives," Nucleic Acids Research, 19:1527-1532, 1991.
Balgobin et al., "Solid Phase Synthesis of DNA Under a Non-Depurinative Condition With a Base Labile 5'-Protecting Group (Fmoc) using Phosphiteamidite Approach," Nucleosides and Nucleotides, 6:461-463, 1987.
Beaucage et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach," Tetrahedron, 48:2223-2311, 1992.
Bellon et al., "4'-Thio-oligo-.beta.-D-ribonucleotides: synthesis of .beta.-4'-thio-oligouridylates, nuclease resistance, base pairing properties, and interaction with HIV-1 reverse transcriptase," Nucleic Acids Res., 21:1587-1593, 1993.
Cormier et al., "Synthesis of hexanucleotide analogues containing diisopropylsilyl internucleotide linkages," Nucleic Acids Research, 16:4583-4594, 1988.
Damha et al., "An improved procedure for derivatization of controlled-pore glass beads for solid-phase oligonucleotide synthesis," Nucleic Acids Research, 18:3813-3821, 1990.
Jones, R.A., "Preparation of Protected Deoxyribonucleosides," Oligonucleotide Synthesis, Gait, ed., Oxford: IRL Press, Chapter 2, 1984.
Li et al., "Synthesis and Characterization of Oligonucleotides Containing 4-O-Methylthymine," Biochemistry, 26:1086-1093, 1987.
Loke et al., "Delivery of c-myc Antisense Phosphorothioate Oligodeoxynucleotides to Hematopoietic Cells in Culture by Liposome Fusion: Specific Reduction in c-myc Protein Expression Correlates with Inhibition of Cell Growth and DNA Synthesis," Top. Microbiol. Immunol., 141:282-289, 1988.
Ma et al., "The 9-Fluorenylmethyloxycarbonyl Group as a 5'-OH Protection in Oligonucleotide Synthesis," Biopolymers, 28:965-993, 1989.
Marcus-Sekura et al., "Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages," Nucleic Acids Research, 15:5749-5763, 1987.
Matteucci, "Deoxyoligonucleotide Analogs Based on Formacetal Linkages," Tetrahedron Letters, 31:2385-2388, 1990.
Mazur et al., "Isosteres of Natural Phosphates. 11. Synthesis of a Phosphonic Acid Analogue of an Oligonucleotide," Tetrahedron, 40:3949-3956, 1984.
Miller et al., "Effects of a Trinucleotide Ethyl Phosphotriester, G.sup.m p (Et)G.sup.m p(Et)U, on Mammalian Cells in Culture," Biochemistry, 16:1988-1996, 1977.
Nair, "Regiospecific 5'-Silylation of Nucleosides," Org. Prep. Proc. Int., 22:57-61, 1990.
Robins et al., "Nucleic Acid Related Compounds. 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Stereoselective Conversation of Ribonucleosides to 2'-Deoxynucleosides," J. Am. Chem. Soc., 105:4059-4065, 1983.
Stirchak et al., "Uncharged Stereoregular Nucleic Acid Analogues. 1. Synthesis of a Cytosine-Containing Oligomer with Carbamate Internucleoside Linkages," J. of Organic Chemistry, 52:4202-4206, 1987.
Wilson, "Cellular Transport Mechanisms," Ann. Rev. Biochem., 47:933-965, 1978.
Wright et al., "Large Scale Synthesis of Oligonucleotides via Phosphoramidite Nucleosides and a High-loaded Polystyrene Support," Tetrahedron Letters, 34:3373-3376, 1993.
Coull et al., Tetrahedron Letters, vol. 28, No. 7, pp. 745-748, (1987).
Goodchild, Bioconjugate Chemistry, vol. 1, No. 3, pp. 165-187, (1990).
Stirchak et al., J. Org. Chem. vol. 52, pp. 4202-4206, (1987).

Affiliated with

Also associated with

Rating

Backbone modified oligonucleotide analogs and solid phase synthe does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Backbone modified oligonucleotide analogs and solid phase synthe, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Backbone modified oligonucleotide analogs and solid phase synthe will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1659804