Backbone modified oligonucleotide analogs and preparation thereo

Details Backbone modified oligonucleotide analogs and preparation thereo Backbone modified oligonucleotide analogs and preparation thereo

1997-02-04

1999-10-19

Marschel, Ardin H.

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

Organic compounds

Carbohydrates or derivatives

536 231, 536 2854, 536 253, C07H 1900, C07H 2102, C07H 1906, C07H 2100

Patent

active

059691182

ABSTRACT:
Methods for preparing oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. In preferred embodiments, the methods involve radical coupling of 3'- and 5'-substituted or 5'- and 3'-subutituted nucleosidic synthons.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan, Jr. et al.
patent: 4997924 (1991-03-01), Jarvi et al.
patent: 5174962 (1992-12-01), Brennan
patent: 5235033 (1993-08-01), Summerton et al.
patent: 5378825 (1995-01-01), Sanghvi et al.
Abdel-Magid et al., "Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride,".
Egholm et al., Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide.
Giannis et al., "Fragmentation and Wittig Olefination of Glucosamine Derivatives--A Simple Route to Open Chain Amino Sugars and Chiral Glyerols," Tetrahedron, 44:7177-7180, 1988.
Goodchild, Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and.
Greene et al., Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., 1991, pp. 175-223.
Horwitz et al., "Nucleotides. V. The Nonomesylates of 1-(2'-Deoxy-.beta.-D-lynofuranosyl) thymine," J. Org. Chem., 29:2076, 1964.
Hyrup et al., "Modification of the Binding Affinity of Peptide Nucleic Acids (PNA). PNA with Extended Backbones consisting of 2-Aminoethyl-.beta.-alanine or 3-Aminopropylglycine Units," J. Chem. Soc. Chem. Comm.
Inouye et al., "Selective Coloration of Spiro Pyridopyrans for Guanosine Derivatives," J. Am. Chem.
Jenkins et al., "9-(2-Methyl-.beta.-D-ribofuranosyl) adenine (2'-Methyladenosine," Synthetic Procedures in Nucleic.
Lin et al., "Synthesis and Biological Activity of Several Amino Analogues of Thymidine," J. Med. Chem., 21:109-112, 1978.
Ma et al., "Design and synthesis of RNA miniduplexes via a synthetic linker approach. 2. Generation of covalently closed, double-stranded cyclic HIV-1 TAR RNA analogs with high Tat-binding affinity," Nucleic.
Matsuda et al., Synthesis and Biological Activities of 3'-Deoxy-3'-Isocyano,-Isothiocyano, and -Isoselenocyano-.
Nair et al., "Regiospecific 5'-Silylation of Nucleosides," Org. Prep. Procedures Int., 22:57-61, 1990.
Pauling, "Molecular Architecture and Biological Reactions," Chem. Eng. News, 24:1375-1377, 1946.
Perkins et al., "Accelerated Displacement of Duplex DNA Strands by a Synthetic Circular Oligodeoxynucleotide,".
Poopeiko et al., "A Simple Method for Azido Group Reduction," Syn. Lett., 342, 1991.
Prakash et al., Molecular Recognition by Circular Oligonucleotides. Strong Binding of Single-stranded DNA.
Rebek, Jr., "Molecular Recognition and Biophysical Organic Chemistry," Ace. Chem. Res., 23:399-404, 1990.
Rentzeperis et al., Contribution of Loops and Nicks to the Formation of DNA Dumbbells: Melting Behavior and.
Sanghvi et al., "Synthesis and Structure of Methylene(dimethylhydrazo) Linked Thymidine Dimer and Their Utility as Antisense Oligonucleotides," Collect. Czech. Chem. Commun., 58:158-162, 1993.
Secrist et al., Abstract 21, "Synthesis and Biological Activity of 4'-Thionucleosides," Program & Abstracts, Tenth International Roundtable, Nucleosides, Nucleotides and their Biological Applications, Park City.
Sproat et al., "2'-O-Methyloligoribonucleotides: Synthesis and Applications," Oligonucleotides and Analogs A Practical Approach, F. Eckstein Ed., IRL Press, p. 55, 1991.
Trapani et al., "N-1-Alkenyl-N,S-Diacyl-2-Aminobenzenethiols (Enamides) by Ring-Opening of 2,3-Dihydro-1,3-benzothiazoles with Aliphatic Carboxylic Anhydrides," Synthesis, 84, 1988.
Trost et al., ed., Comprehensive Organic Synthesis, vol. 4, pp. 758-776, 1991.
Tuladhar et al., "A Synthetic Route to Poly-N,N'-Dimethylethylenediamines," Tet. Letts., 33:2203-2206, 1992.
Yamamoto et al., "One-Step Synthesis of 5'-Azido-nucleosides," J. Chem. Soc. Perkin I, 306-310, 1980.
Zuckermann et al., "Efficient Method for the Preparation of Peptoids [Oligo(N-substituted glycines)] by Submonomer Solid-phase Synthesis," J. Am. Chem. Soc., 114:10646-10647, 1992.
Puglisi et al., "Absorbance Melting Curves of RNA," Methods in Enzymology, 180:304-325, 1989.
Kool et al. J. Chem. Soc. Chem. Commun. 1991 1161.
Morr et al. Building Blocks for the Chemical Synthesis of DNA Containing C(3')-CH2-P Bonds in Chemical Synthesis in Nolecular Biology GBF (Gesellschaft fueunsch Biotecnolgiesche Forschung Branweig-Stoeckheim) Bloecker et al. eds. 987 8:107-113.
Grant et al. Hackh's Chemical Dictionary 4th. Ed. McGraw-Hill NY 1969 pp. 27,466,569, and 575.
MacCoss et al. "A new synthetic use of nucleoside N-oxides" J. Org. Chem., vol. 45, pp. 788-794, 1980.
Griengl et al. "5-(Haloalkyl)-2'-deoxyuridines: A novel type of potent antiviral nucleoside analogue" J. Med. Chem. vol. 28, pp. 1679-1684, 1985.
Cushley et al. "Nucleosides. XLIX. Nuclear magnetic resonance studies of 2'- and 3'-halogeno nucleosides. The conformations of 2'-deoxy-2'fluorouridine and 3'-deoxy-3'-fluoro- -D-arabinofuranosyluracyl" Canadian Journal of Chemistry, vol. 46, pp. 1131-1111, 1968.
Bankston et al., "A Short Synthesis of 5'-O-Tritryl-Protected threo- and erythro- 3'-Cyano-3'-doexythymidine Epimers Using Free-Radical Chemistry," J. Het. Chem., 29:1405-1407, 1992.
Barton et al., "A "One-Pot" Synthesis of Sulfenamides," J. Org. Chem., 56:6702-6704,, 1991.
Barton et al., "Stereoselectivity in Radical Reactions of 2'-Deoxynucleosides. A Synthesis of an Isostere of 3'-Azido-3'-Deoxythymidine-5'-Monophosphate," Tetrahedron Letters, 30:4969-4972, 1989.
Baud et al, "Improved Procedure for the Regiospecific Synthesis of 2'-Deoxyribonucleosides," Tetrahedron Letters, 31:4437-4440, 1990.
Beaucage et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach," Tetrahedron, 48:2223-2311, 1992.
Bodenteich et al., "Synthesis of Enantiomerically Pure Carbocyclic 3'-Azido-2',3'-Dideoxythymidine, A Potential Anti-Aids Drug," Tetrahedron Letters, 28:5311-5312, 1987.
Camarasa et al., "Aldol Reaction of Nucleoside 5'-Carboxaldehydes with Acetone, Synthesis of 5'-C-Chain Extended Thymidine Derivatives," Nucleosides and Nucleotides, 9:533-546, 1990.
Cormier et al., "Synthesis of hexanucleotide analogues containing diisopropylsilyl internucleotide linkages," Nucleic Acids Research, 16:4583-4594, 1988.
Cosstick et al., "Synthesis and properties of dithymidine phosphate analogues containing 3'-thiothymidine," Nucleic Acids Res., 18:829-835, 1990.
Debart et al., "Intermolecular Radical C--C Bond Formation: Synthesis of a Novel Dinucleoside Linker for Non-anionic Antisense Oligonucleotides," Tet. Lett., 33:2645-2648, 1992.
Etzold et al., "The Extension of the Sugar Chain of Thymidine: a New Route to 5'-Deoxyhexose Nucleosides," J.C.S. Chem. Comm., 422, 1968.
Fiandor et al., "Synthesis of 3'-deoxy-3'-(2-propynyl)thymidine and 3'-cyanamethyl-3'-deoxythymidine, analogs of AZT," Tet. Lett., 31:597-600, 1990.
Fikes et al., "Preassociating .alpha.-Nucleophiles," J. Am. Chem. Soc., 114:1493-1496, 1992.
Fleet et al., "Methyl 5-O-Tert-Butyldiphenylsilyl-2-.alpha..beta.-D-Threo-Pentofuranoside as a Divergent Intermediate for the Synthesis of 3'-Substituted-2',3'-Dideoxynucleosides: Synthesis of 3'-Azido-3'-Deoxythymidine, 3'-Deoxy-3'-Fluorothymidine and 3'-Cyano-3'-Deoxythymidine," Tetrahedron, 44:625-636, 1988.
Gait, M.J., ed., Oligonucleotide Synthesis, A Practical Approach. Washington, D.C.: IRL Press, 1984, Chapter 3, pp. 35-81.
Hanamoto et al., "SmI.sub.2 -Promoted Ketyl Radical Addition to O-Benzyl Formaldoxime. A New Aminomethylation," Tet. Letts. 32:3555-3556, 1991.
Hart et al., "Bis(trimethylstannyl) benzopinacolate-Mediated Intermolecular Free-Radical Carbon--Carbon Bond-Forming Reactions: A New One-Carbon Homologation," J. Am. Chem. Soc., 110:1631-1633, 1988.
Hillgartner et al., "Bix(trimethylzinn)benzpinakolat, seine reversible radikalische Dissoziation und Reaktionen," Liebigs. Ann. Chem., 586-599, 1975.
Hronowski et al., "Synthesis of New Carbocyclic Analogues of 3'-Azido- and 3'-Amino-2',3'-dideoxynucleosides," J. Chem. Soc., Chem. Commun., 1547-1548, 1990.
Jones et al., "The Synthesis of 6'-Deoxyhomonucleoside-6'-pho

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