Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen bonded directly to ring carbon of the purine ring...
Patent
1995-06-07
2000-10-17
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen bonded directly to ring carbon of the purine ring...
544277, 544317, C07D47318, C07D47340, C07D47334, C07D23947
Patent
active
061334448
ABSTRACT:
A method is disclosed for preparing novel purine PNA synthons having protecting groups which may be removed under mild conditions. The purine PNA synthons generally are prepared by coupling purine derivatives having carbamate protection to a protected N-(2-aminoethyl)-glycine backbone. By a method of this invention, purine PNA synthons may have orthogonal protection of the carbamate protected purine and the protected backbone. The purine PNA synthons are useful in the synthesis of peptide nucleic acids (PNAs) and other oligomers such as PNA-DNA chimeras, and may be used in automated synthesizers. In practicing methods of the invention, novel compositions of matter also are disclosed. For example, disclosed herein are an adenine PNA synthon having the following formula: ##STR1## and a guanine PNA synthon having the following formula: ##STR2##
REFERENCES:
patent: H725 (1990-01-01), Gordon
patent: 3852332 (1974-12-01), Cross
patent: 3936452 (1976-02-01), Nagasawa
patent: 4001226 (1977-01-01), Spry
patent: 4450164 (1984-05-01), Bristol et al.
patent: 4477441 (1984-10-01), Boger et al.
patent: 4514391 (1985-04-01), Gordon et al.
patent: 4548926 (1985-10-01), Matsueda et al.
patent: 4599198 (1986-07-01), Hoover
patent: 4616088 (1986-10-01), Ryono et al.
patent: 4668769 (1987-05-01), Hoover
patent: 4668770 (1987-05-01), Boger et al.
patent: 4757050 (1988-07-01), Natarajan et al.
patent: 4880938 (1989-11-01), Freidinger
patent: 4933431 (1990-06-01), Domb
patent: 4963530 (1990-10-01), Hemmi et al.
patent: 4977277 (1990-12-01), Rosenberg et al.
patent: 5264586 (1993-11-01), Nicolaou
patent: 5340716 (1994-08-01), Ullman
patent: 5424451 (1995-06-01), Alisi
patent: 5455354 (1995-10-01), Wong
Ege, "Organic Chemistry, Third Edition", pp. 114, 591, 592, 1994.
Adamiak et al., "A Highly Effective Route to N,N.sup.1 -Disubstituted Ureas Under Mild Conditions. An Application to the Synthesis of tRNA Anticodon Loop Fragments Containing Ureidonucleosides," Tetrahedron Letters, 22:1935-1936 (1977).
Almarsson et al., "Peptide Nucleic Acid (PNA) Conformation and Polymorphism in PNA-DNA and PNA-RNA Hybrids," Proc. Natl. Acad. Sci. USA, 90:9542-9546 (1993).
Almarsson et al., "Molecular Mechanics Calculations of the Structures of Polyamide Nucleic Acid DNA Duplexes and Triple Helical Hybrids," Proc. Natl. Acad. Sci. USA, 90:7518-7522 (1993).
Ambrosius et al., "Peptide Analogues of the Anaphylatoxin C3a; Syntheses and Properties," Biol. Chem. Hoppe-Seyler, 370:217-227 (1989).
Barany et al., "A Three-Dimensional Orthogonal Protection Scheme for Solid-Phase Peptide Synthesis Under Mild Conditions," J. Am. Chem. Soc., 107:4936-4942 (1985).
Barcelo et al., "Alkyl-1-Chloroalkyl Carbonates: Reagents for the Synthesis of Carbamates and Protection of Amino Groups," Synthesis, 8:627-632 (1986).
Briepohl et al., "Preparation and Use of FMOC-Protected Building Blocks for the Synthesis of Peptide Nucleic Acids (PNA'S)," presented at 1st Australian Peptide Conference, Daydream Island, Great Barrier Reef, Australia, Oct. 16-21, 1994.
Chen et al., "Molecular Dynamics and NMR Studies of Single-Stranded PNAs," Tetrahedron Letters, 35:5105-5108 (1994).
Cherny et al., "DNA Unwinding Upon Strand-Displacement Binding of a Thymine-Substituted Polyamide to Double-Stranded DNA," Proc. Natl. Acad. Sci. USA, 90:1667-1670 (1993).
Chheda et al., "Synthesis of Naturally Occurring 6-Ureidopurines and Their Nucleosides," Journal of Medicinal Chemistry, 14:748-753 (1971).
Chollet et al., "Biotin-Labeled Synthetic Oligodeoxyribonucleotides: Chemical Synthesis and Uses as Hybridization Probes," Nucleic Acids Research, 13:1529-1541 (1985).
Christensen et al., "Improved Synthesis, Purification and Characterization of PNA Oligomers," Solid Phase Synthesis, collected papers from Third International Symposium, Oxford, England, Aug. 31-Sep. 4, 1993 (1994).
Christensen et al., "Optimized Solid-Phase Synthesis of PNA Oligomers," Thirteenth American Peptide Symposium, Edmonton, Alberta, Canada, Jun. 20-25, 1993, Abstract P7, pp. 2-22.
Coull et al., "Optimized Solid-Phase Synthesis of PNA Oligomers," Solid Phase Synthesis, Lecture Programme and Abstract Book Abstract 5a.2, p. 17, Aug. 31-Sep. 4, 1993, U. of Oxford, UK.
Demidov et al., "Sequence Selective Double Strand DNA Cleavage by Peptide Nucleic Acid (PNA) Targeting Using Nuclease S1," Nucleic Acids Research, 21:2103-2107 (1993).
Dueholm et al., "An Efficient Synthesis of BOC-Aminoacetaldehyde and Its Application to the Synthesis of N-(2-BOC-Aminoethyl)Glycine Esters," Organic Preparations and Procedures Int., 25(4):457-461 (1993).
Dueholm et al., "Peptide Nucleic Acid (PNA) with a Chiral Backbone Based on Alanine," Bioorganic & Medicinal Chemistry Letters, 4:1077-1080 (1994).
Dueholm et al., "Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization," J. Org. Chem., 59:5767-5773 (1994).
Egholm et al., "Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone," J. Am. Chem. Soc., 114:1895-1897 (1992).
Egholm et al., "Recognition of Guanine and Adenine in DNA by Cytosine and Thymine Containing Peptide Nucleic Acids (PNA)," J. Am. Chem. Soc., 114:9677-9678 (1992).
Egholm et al., "PNA Hybridizes to Complementary Oligonucleotides Obeying the Watson-Crick Hydrogen-Bonding Rules," Nature, 365:566-568 (1993).
Fuller et al., "Urethane-Protected Amino Aicd N-Carboxy Anhydrides and Their Use in Peptide Synthesis," J. Am. Chem. Soc., 112:7414-7416 (1990).
Hanvey et al., "Antisense and Antigene Properties of Peptide Nucleic Acids," Science, 258:1481-1485 (1992).
Hodge et al., "Synthesis of 1- and 1,2,2'-Deuteriated Deoxyribose and Incorporation into Deoxyribonucleosides," J. Org. Chem., 56:1553-1564 (1991).
Hyrup et al., "Modification of the Binding Affinity Nucleic Acids (PNA). PNA with Extended Backbones consisting of 2-Aminoethyl-.beta.-alanine or 3-Aminopropylglycine Units," J. Chem. Soc., Chem. Commun., 518-519 (1993).
Kates et al., "A Novel, Convenient, Three-Dimensional Orthogonal Strategy for Solid-Phase Synthesis of Cyclic Peptides," Tetrahedron Letters, 34:1549-1552 (1993).
Kates et al., "Solid-Phase N-Glycopeptide Synthesis Using Allyl Side-Chain Protected Fmoc-Amino Acids," Tetrahedron Letters, 35:1033-1034 (1994).
Kingsbury et al., "The Use of Allylic Esters and Carbamates as Protecting Groups in the Synthesis of 5-Substituted Uracil Peptide Analogs," Abstracts of Papers, Abstract No. 216, 188th ACS National Meeting, Philadelphia, Pennsylvania, Aug. 26-31, 1984.
Kosynkina et al., "A Convenient Synthesis of Chiral Peptide Nucleic Acid (PNA) Monomers," Tetrahedron Letters, 35:5173-5176 (1994).
Letsinger et al., "Protecting Groups for Nucleosides Used in Synthesizing Oligonucleotides," J. Am. Chem. Soc., 91:3356-3359 (1969).
Lyon et al., "Reaction Between 2',3',5'-Tri-O-acetyladenosine and Aryl Chloroformates. 2',3',5'-Tri-O-acetyl-N(6)-phenoxycarbonyladenosine as an Intermediate in the Synthesis of 6-Ureidopurine Ribosides," J.C.S., Perkin I, 1978:131-137 (1978).
Meier et al., "Peptide Nucleic Acids (PNAs)-Unusual Properties of Nonionic Oligonucleotide Analogues," Angew Chem. Int. Ed. Engl., 31:1008-1010 (1992).
Nielsen et al., "Sequence-Selective Recognition of DNA by Strand Displacement with a Thymine-Substituted Polyamide," Science, 254:1497-1500 (1991).
Nielson et al., "Sequence Specific Inhibition of DNA Restriction Enzyme Cleavage by PNA," Nucleic Acids Research, 21:197-200 (1993).
Nielson et al., "Sequence-Selective Recognition of DNA by Peptic Nucleic Acid Chimerae (PNA)," Clinical Chemistry, 39:715 (1993).
.O slashed.rum et al., "Single Base Pair Mutation Analysis by PNA Directed PCR Clamping," Nucleic Acids Research, 21:5332-5336 (1993).
PerSeptive Biosystems, "Identifying Point Mutations by PNA-Directed PCR Clamping," Practical PNA, vol. 1, Issue 1 (1995).
PerSeptive Biosystems, "PNA Oligomers as Hybridization Probes," Practical PNA, vol. 1, Issue 2 (1995).
Reese et al., "Some Observations Relating to the Oximate Ion Promoted Unblocking of Olignucleotide Aryl Est
Coull James M.
Egholm Michael
Hodge Richard P.
Ismail Mohamed
Rajur Sharanappa B.
Berch Mark L.
PerSeptive Biosystems Inc.
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