Oligonucleotides having R.sub.p and S.sub.p linkages at predeter

Details Oligonucleotides having R.sub.p and S.sub.p linkages at predeter Oligonucleotides having R.sub.p and S.sub.p linkages at predeter

1993-08-18

1999-03-16

Robinson, Douglas W.

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

Organic compounds

Carbohydrates or derivatives

536 243, 536 245, C07H 2102, C07H 2104

Patent

active

058832378

ABSTRACT:
Methods and compounds are provided for solid phase synthesis of oligonucleotides and related polymers by condensing protected 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 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
Maniatis et al., Molecular Cloning--A Laboratory Manual, Cold Spring Harbor Laboratory, Cold Spring Harbor, NY, 1982, only pp. 197-197 supplied.
Eckstein (IV), "A Dinucleoside Phosphorothioate," Tetrahedron Letters, (13), 1157-1160 1967).
Eckstein (V), "Di-uridin-3',5'-thiophosphate," Tetrahedron Letters, (36), 3495-3499 (1967).
Gura, "Antisense Has Growing Pains--Efforts to Develop Antisense Compounds as Therapies for Cancer, AIDS, and Other Diseases Have Encountered Some Unexpected Questions About How the Drugs Really Work," Science, 270, 575-577 (1995).
Cossick et al.(I), "An Approach to the Stereoselective Synthesis of S.sub.p -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(O,O)-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).
Cossick 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," Science, 165, 1137-1139 (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 Polyribonucleotide Containing Alternating ->P=O and ->P=S Linkages," Eur. J. Biochem., 3(4), 448-452 (1968).
Cruse et al., "Chiral Phosphorothioate Analogues of B-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 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 Configuration of Rp and Sp Diastereomers of an Ethyl Phosphotriester (Et) Modigied EcoRi Recognition Sequence, 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. application No. 07/463,358, filed Jan. 11, 1990.
Cook, U.S. application No. 07/566,977, filed Aug. 13, 1990.
Brody et al., Unambiguous Determination of the Stereochemistry of Nucleotidyl Transfer Catalyzed by DNA Polymerase I from Escherichia coli, Biochemistry 20:1245-1252 (1981).
Brody et al., Stereochemical Course of Nucleotidyl Transfer Catalyzed by Bacteriophage T7 Induced DNA Polymerase.dagger., American Chemical Society, pp. 2570-2572 (1982).
Burgers et al., Synthesis of Dinucleoside Monophosphorothioates Via Addition of Sulphur to Phosphite Triesters, Tetraheron Letters, No. 40:3835-3838 (1978).
Connolly et al., Synthesis and Characterization of an Octanucleotide Containing the EcoRI Recognitio

Affiliated with

Also associated with

Rating

Oligonucleotides having R.sub.p and S.sub.p linkages at predeter does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Oligonucleotides having R.sub.p and S.sub.p linkages at predeter, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oligonucleotides having R.sub.p and S.sub.p linkages at predeter will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-818776