Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-06-05
1997-07-08
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 251, 536 252, 536 253, 536 231, C07H 2102, C07H 2104
Patent
active
056462670
ABSTRACT:
Methods and compounds are provided for solid phase synthesis of oligonucleotides and related polymers by condensing protected monomer-O-[1,3,2-dichalcogen-substituted-phospholane] synthons in the presence of a catalytic base. Compounds of the invention include 2-N-substituted-1,3,2-dichalcogen-substituted-phospholane precursors of the above synthons, the protected monomer-O-[1,3,2-dichalcogen-substituted-phospholane] synthons, and P-chiral oligonucleotides and related P-chiral polymers.
REFERENCES:
patent: 3687808 (1972-08-01), Merigan et al.
patent: 3846402 (1974-11-01), Eckstein et al.
patent: 4647529 (1987-03-01), Rodland et al.
patent: 4806463 (1989-02-01), Goodchild et al.
patent: 5112963 (1992-05-01), Pieles et al.
patent: 5135917 (1992-08-01), Burch
patent: 5194428 (1993-03-01), Agrawal et al.
patent: 5212295 (1993-05-01), Cook
patent: 5248670 (1993-09-01), Draper et al.
patent: 5264423 (1993-11-01), Cohen et al.
patent: 5271941 (1993-12-01), Cho-Chung
patent: 5276019 (1994-01-01), Cohen et al.
patent: 5334711 (1994-08-01), Sproat et al.
patent: 5521302 (1996-05-01), Cook
Cosstick et al.(I), "An Approach to the Stereoselective Synthesis of Sp-dinucleoside Phosphorothioates Using Phosphotriester Chemistry," Nucleic Acids Res., 15(23), 9921-9932 (1987).
Slim et al., "Conformationally Defined Phosphorothioate-Containing Oligoribonucleotides in the Study of the Mechanism of Cleavage of Hammerhead Ribozymes," Nucleic Acids Res., 19(6), 1183-1188 (1991).
Stec et al.(I), "Reverse-Phase High-Performance Liquid Chromatographic Separation of Diastereomeric Phosphorothioate Analogues of Oligodeoxyribonucleotides and Other Backbone-Modified Congeners of DNA," J. Chromatography, 326, 263-280 (1985).
Stec et al.(II), "Novel Route to Oligo(Deoxyribonucleoside Phosphorothioates), Stereocontrolled Synthesis of P-Chiral Oligo(Deoxyribonucleoside Phosphorothioates)," Nucleic Acids Res., 19(21), 5883-5888 (1991).
Stec et al.(III), "Automated Solid-Phase Synthesis, Separation, and Stereochemistry of Phosphorothioate Analogues of Oligodeoxyribonucleotides," J. Am. Chem. Soc., 106(20), 6077-6079 (1984).
Stec et al.(IV), "Solid-Phase Synthesis, Separation, and Stereochemical Aspects of P-Chiral Methane- and 4,4'-Dimethoxytriphenylmethanephosphonate Analogues of Oligodeoxyribonucleotides," J. Org. Chem., 50, 3905-3913 (1985).
Stec et al.(V), "Synthesis, Separation, and Stereochemistry of Diastereoisomeric Oligodeoxyribonucleotides Having a 5'-Terminal Internucleotide Phosphorothioate Linkage," Tetrahedron Lett., 25(46), 5275-5278 (1984).
Lesnikowski et al.(I), "Stereoselective Synthesis of P-Homochiral Oligo(thymidine Methanephosphonates," Nucleic Acids Res., 16(24), 11675-11689 (1988).
Lesnikowski et al.(II), "Octa(thymidine methanephosphonates) of Partially Defined Stereochemistry: Synthesis and Effect of Chirality at Phosphorus on Binding to Pentadecadeoxyriboadenylic Acid," Nucleic Acids Res., 18(8), 2109-2115 (1990).
Lesnikowski et al.(III), "Studies on Stereospecific Formation of P-Chiral Internucleotide Linkage. Synthesis of (Rp, Rp)- and (Sp,Sp)- thymidylyl(3',5')thymidine di(0,0)-phosphorothioate) Using a 2-Nitrobenzyl Group as a New S-Protection," Tetrahedron Lett., 30(29), 3821-3824 (1989).
Lesnikowski et al.(IV), "Studies on Stereospecific Formation of P-Chiral Internucleotide Linkage. Synthesis of Diastereoisomeric 2'-Deoxyadenylyl(3',5') 2'-Deoxyadenylyl-S-Methylphosphorthioates via Nucleoside Hydroxyl Activation," Tetrahedron, 42(18), 5025-5034 (1986).
Cosstick et al.(II), "Synthesis of d(GC) and d(CG) Octamers Containing Alternating Phosphorothioate Linkages: Effect of the Phosphorothioate Group on the B-Z Transition, " Biochemistry, 24(14), 3630-3638 (1985).
Eckstein(I), "Nucleoside Phosphorothioates," Ann. Rev. Biochem., 54, 367-402 (1985).
Eckstein(II), "Phosphorothioate Analogues of Nucleotides--Tools for the Investigation of Biochemical Processes," Angew. Chem. Intl. Ed., 22(6), 423-506 (1983).
Eckstein(III), "Stabilization of DNA by Incorporation of Phosphorothioate Groups," Nucleosides & Nucleotides, 4(1 & 2), 77-79 (1985).
Eckstein et al.(I), "Polyribonucleotides Containing a Phosphorothioate Backbone," Eur. J. Biochem., 13(3), 558-564 (1970).
Eckstein et al.(II), "Phosphorothioates in Molecular Biology," Trends in Biochemical Science, 14, 97-100 (1989).
Connolly et al.(I), "The Stereochemical Course of the Restriction Endonuclease EcoRI-catalyzed Reaction," J. Biological Chem., 259(17), 10760-10763 (1984).
Connolly et al.(II), "Synthesis and Characterization of an Octanucleotide Containing the EcoRI Recognition Sequence with a Phosphorothioate Group and the Cleavage Site," Biochemistry, 23(15) 3443-3453 (1984).
De Clercq et al., "Interferon Induction Increased through Chemical Modification of a Synthetic Polyribonucleotide," Sciece, 165, 1137-113 (1969).
Ott et al., "Protection of Oligonucleotide Primers against Degradation by DNA Polymerase I," Biochemistry, 26(25), 8237-8241 (1987).
Potter et al., "A Stereospecifically .sup.18 O-labelled Deoxydinucleoside Phosphate Block for Incorporation into an Oligonucleotide," Nucleic Acids Res., 11(20), 7087-7103 (1983).
Spitzer et al., "Inhibition of Deoxyribonucleases by Phosphorothioate Groups in Oligodeoxyribonucleotides," Nucleic Acids Res., 16(24), 11691-11704 (1988).
Matzura et al., "A Polyriboncleotide Containing Alternating ->P=O and ->P=S Linkages," Eur. J. Biochem., 3(4), 448-452 (1968).
Cruse et al., "Chiral Phosphorothioate Analogues of .beta.-DNA. The Crystal Structure of Rp-d.vertline.Gp(S)CpGp(S)CpGp(s)C.vertline.," J. Mol. Biol., 192, 891-905 (1986).
LaPlanche et al., "Phosphorothioate Modified Oligodeoxyribonucleotides. III. NMR and UV Spectroscopic Studies of the Rp-Rp, Sp-Sp, and Rp-Sp Duplexes, [d(GG.sub.3 AATTCC)].sub.2, Derived for Diastereomeric O-Ethyl Phosphorothioates," Nucleic Acids Res., 14(22), 9081-9093 (1986).
Fujii et al., "Acylphosphonates. 7. A New Method for Stereospecific and Stereoselective Generation of Dideoxyribofuranoside Phosphorothioates Via the Acylphosphonate Intermediates," Tetrahedron, 43(15), 3395-3407 (1987).
Gallo et al., "Alkyl Phosphotriester Modified Oligodeoxyribonucletides. V. Synthesis and Absolute Configuraion of Rp and Sp Diastereomers of an Ethyl Phosphotriester (Et) Modified EcoRI Recognition Sequence, d[GGAA(Et)TTCC]. A Synthetic Approach to Regio- and Stereospecific Ethylation-Interference Studies," Nucleic Acids Res., 14(18), 7405-7420 (1986).
Nelson et al., "Synthesis of P-Thioadenylyl-(2'-5')-adenosine and P-Thioadenylyl-(2'-5')-P-Thioadenylyl-(2'-5')-adenosine," J. Org. Chem., 49(13), 2314-2317 (1984).
Brody et al., "Unambiguous Determination of the Stereochemistry of Nucleotidyl Transfer Catalyzed by DNA Polymerase I from Escherichia coli," Biochemistry, 20(5), 1245-1252 (1981).
Marugg et al., "Synthesis of Phosphorothioate-Containing DNA Fragments by a Modified Hydroxybenzotriazole Phosphotriester Approach," Nucleic Acids Res., 12(23), 9095-9110 (1984).
Zon, "Oligonucleotide Analogues as Potential Chemotherapeutic Agents," Pharmaceutical Research, 5(9), 539-549 (1988).
Cook, U.S. Patent Application 07/463,358, filed Jan. 11, 1990.
Cook, U.S. Patent Application 07/566,977, filed Aug. 13, 1990.
Grajkowski Andrzej
Stec Wojciech J.
Uznanski Bogdan
Crane L. Eric
Kight John
Macevicz Stephen C.
Polish Academy of Sciences
LandOfFree
Method of making oligonucleotides and oligonucleotide analogs us does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method of making oligonucleotides and oligonucleotide analogs us, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of making oligonucleotides and oligonucleotide analogs us will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2409507