Chalcophospholanes useful in the synthesis of oligonucleoside ph

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

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 268, 536 2533, C07H 1910, C07H 1920

Patent

active

053590520

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: 5169842 (1992-12-01), Lobberding et al.
Bayever et al., "Guest Editorial: Systemic Human Antisense Therapy Begins", Antisense Res. Development, 2, 109-110 (1992).
Ratajczak et al., "In vivo Treatment of Human Leukemia in a scid Mouse Model with c-myb Antisense Oligodeoxynucleotides", Proc. Nat. Acad. USA, 89, 11823-11827 (1992).
Simons et al., "Antisense c-myb Oligonucleotides Inhibit Intimal Arterial Smooth Muscule Cell Accumulation in vivo", Nature, 359, 67-70 (1992).
Biro et al., "Inhibitory Effects of Antisense Oligodeoxynucleotides Targeting c-myc mRNA on Smooth Muscle Cell Proliferation and Migration", Proc. Nat. Acad. Sci. USA, 90, 654-658 (1993).
Whitesell et al., Stability, clearance, and disposition of intraventricularly administered oligodeoxynucleotides: Implications for therapeutic application within the central nervous system, Proc. Natl. Acad. Sci., 90:4665-4669 (1993).
Aragawal et al., Pharmacokinetics, biodistribution, and stability of oligodeoxynucleotide phosphorothioates in mice, Proc. Natl. Acad. Sci., 88:7595-7599 (1991).
Iverson, In vivo studies with phosphorothioate oligonucleotides: pharmacokinetics prologue, Anti-Cancer Drug Design, 6:531-538 (1991).
Skorski et al., Suppression of Philadelphia leukemia cell growth in mice by CR-A antisense oligonucleotides, Proc. Natl. Acad. Sci., 91:4504-4508 (1984).
Bloch, Ann. New York Acad. Sci., vol. 255 (1975), Chemistry, biology, and clinical uses of nucleoside analogs.
Scheit, pp. 1-61 in Nucleotides Analogs (Wiley-Interscience, New York, 1993), Chapter 1 entitled "Chemical Structure of Nucleotides" and excerpt from chapter 2 entitled Nucleotides with modified heterocyclic substituents.
Kornberg and Baker, DNA Replication, Second Edition (Freeman, New York, 1992), Section 14-3 entitled "Nucleotides analogs incorporated into DNA or RNA".
Hurst, An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines (John Wiley, New York, 1980), Chapter 2: The Chemistry of Pyrimidines, Chapter 3: The Chemistry of Purines and Pteridines.
Kudelska et al., "Reaction of Sugar Epoxides with Phosphorothioic Acids, Evidence of the Pentacoordinate Phosphorus Intermediate in the Reaction of 5,6-anhydro-1,2-O-isopropylidene-.alpha.-D-glucofuranose with Phosphorothioic Acid", Tetrahedron, 42(2), 629-636 (1986).
Michalska et al., "Mechanistic and Synthetic Aspects of Intramolecular Base-Catalyzed Migration of the Thiophosphoryl Group from Sulfur to Oxygen in Sugar .beta.-Hydroxyphosphorodithioate Systems", J. Am. Chem. Soc., 113, 7945-7951 (1991).
Stec et al., "Novel Route to Oligo(Deoxyribonucleoside Phosphorothioates), Stereocontrolled Synthesis of P-Chiral Oligo(Deoxyribonucleoside Phosphorothioates)", Nucl. Acids Res., 19(21), 5883-5888 (1991).
Cosstick et al., "An Approach to the Stereoselective Synthesis of S.sub.p -dinucleoside Phosphorothioates Using Phosphodiester Chemistry", Nucl. Acids Res., 15(23), 9921-9932 (1987).
Stec et al., "Reverse-Phase High-Performance Liquid Chromatographic Separation of Diasteromeric Phosphorothioate Analogues of Oligodeoxyribonucleotides and Other Backbone-Modified Congeners of DNA", J. Chromatography, 326, 263-280 (1985).
Lesnikowski et al., "Stereoselective Synthesis of P-homochiral Oligo(thymidine Methanephosphonates", Nucl. Acids Res., 16(24), 11675-11689 (1988).
Slim et al., "Conformationally Defined Phosphorothioate-containing Oligoribonucleotides in the Study of the Mechanism of Cleavage of Hammerhead Ribozymes", Nucl. Acids Res., 19(6), 1183-1188 (1991).
Lesnikowski et al., "Octa(thymidine methanephosphonates) of Partially Defined Stereochemistry: Synthesis and Effect of Chirality at Phosphours on Binding to Pentadecadeoxyriboadenylic Acid", Nucl. Acids Res., 18(8), 2109-2115 (1990).
Fujii et al., "Acylphosphonates. 7. A New Method for Sterospecific and Stereoselective Generation of Dideoxyribofuranoside Phosphorothioates Via the Acylphosphonate Intermediates", Tetrahedron, 43(15), 3395-3407 (1987).
Willson et al., "Etude du Mecanisme des Reactions D'acidolyse D'alcoolyse et D'aminolyse des Oxathiaphospholanes-1,3,2", Bull. Soc. Chim. Fr., 5.sup.e Serie, 1975, 615-620.
Thuong et al., "Nouvelle Methode des Preparation D'esters Phosphorique, Renformant un Groupe .beta.-mercaptoethyle, Utilinables en Synthese Nucleotidique", Bull. Soc. Clim. Fr., Part II, 1981 (Jan.-Feb.), 52-56.
Dahl et al., "Mechananistic Studies on the Phosphoramidite Coupling Reaction in Oligonucleotide Synthesis. I. Evidence for Nucleophilic Catalysis by Tetrazole and Rate Variations with Phosphorus Substituents", Nucl. Acids Res., 15(4), 1729-1743 (1987).
Richter et al., "A Programmed Five-membered Cyclic Phosphorylating Reagent for the Synthesis of Oligonucleotides and Its Use", Tetrahedron, 46(9), 3167-3712 (1990).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Chalcophospholanes useful in the synthesis of oligonucleoside ph does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Chalcophospholanes useful in the synthesis of oligonucleoside ph, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chalcophospholanes useful in the synthesis of oligonucleoside ph will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-136403

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.