Chiral peptide nucleic acid monomers and oligomers

Details Chiral peptide nucleic acid monomers and oligomers Chiral peptide nucleic acid monomers and oligomers

1994-12-28

1999-11-02

Marschel, Ardin H.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

435 6, 435 691, 436501, 514 2, 514 44, 530317, 530350, 935 77, 935 78, C07K 502, C07K 508, C07K 702, C12Q 168

Patent

active

059772964

ABSTRACT:
A novel class of peptide nucleic acid monomers are synthesized having chirality in the backbone. Peptide nucleic acid oligomers are synthesized to incorporate these chiral monomers.

REFERENCES:
patent: 5340716 (1994-08-01), Ullman et al.
Akashi, M. and Takemoto, "New Aspects of Polymer Drugs", Advances in Polymer Science 1990, 97, 107-146.
Almarsson, O. et al., "Molecular Mechanics Calculations of the Structures of Polyamide Nucleic Acid DNA Duplexes and Triple Helical Hybrids", PNAS USA 1993, 90, 7518-7522.
Almarsson, O. et al., "Peptide Nucleic Acid (PNA) Conformation and Polymorphism in PNA-DNA and PNA-RNA Hybrids", PNAS USA 1993, 90, 9542-9546.
Brady, S.F. et al., "Large-scale synthesis of a cyclic hexapeptide analogue of somatostatin", J. Org. Chem. 1987, 52, 764-769.
Brown, S. et al., "NMR Solution Structure of a Peptide Nucleic Acid Complexed with RNA", Science 1994, 265, 777-780.
Buttrey, J. et al., "Synthetic analogues of polynucleotides-XII: the resolution of DL-.beta.-(thymin-1-YL)alanine and polymerisation of the .beta.-(thymin-1-YL) alanines", Tetrahedron 1975, 31, 73-75.
Chen, S. et al, "Molecular Dynamics and NMR Studies of Single-Stranded PNAs", Tetrahedron Letters 1994, 35(29), 5105-5108.
De Koning, H. and Pandit, "Unconventional Nucleotide Analogues. V. Derivatives of 6-(1-pyrimidinyl)-and 6-(9-purinyl)-2-aminocaproic Acid", Recueil 1971, 90, 874-884.
Demidov, Vadim et al., "Sequence Selective Double Strand DNA Cleavage by Peptide Nucleic Acid (PNA) Targeting Using Nuclease S1" Nucl. Acids Res. 1993 21(19), 2103-2107.
Doel et al., "An Approach to the Synthesis of Peptide Analogues of Oligonucleotides (Nucleopeptides)", Tetrahedron Letters 1969, 27, 2285-2288.
Doel et al., "The Synthesis of Peptides Containing Purine and Pyrimidine Derivatives of DL-Alanine", Tetrahedron 1974, 30, 2755-2759.
Dueholm, K. et al., "An Efficient Synthesis of BOC-Aminoacetaldehyde and its Application to the Synthesis of N-(2-BOC-Aminoethyl)glycine Esters", Organic Prep. and Procedures Int. 1993, 25(4), 457-461.
Dueholm, K. et al, "Peptide Nucleic Acid (PNA) with a Chiral Backbone Based on Alanine", Bioorganic & Medicinal Chem. Letters 1994, 4(8), 1077-1080.
Dueholm, K. et al, "Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization", J. of Org. Chem. 1994, 59, 5767-5773.
Egholm, M. "Peptide nucleic acids (PNA). Oligonucleotide analogues with an achiral peptide backbone", J. Am. Chem. Soc. 1992, 114, 1895-1897.
Egholm et al., "PNA Hybridizes to Complementary Oligonucleotides Obeying the Watson-Crick Hydrogen-Bonding Rules", Nature 1993, 365, 566-568.
Flam, F., "Can DNA Mimics Improve on the Real Thing?", Science 1993, 262, 1647-1649.
Frank-Kamenetskii, "A Change of Backbone", Nature 1991, 354, 505.
Griffith, M. et al., "Single and Bis Peptide Nucleic Acids as Triplexing Agents: Binding and Stoichiometry", J. Am. Chem. Soc. 1995, 117, 831-832.
Hanvey, J.C. et al., "Antisense and Antigene Properties of Peptide Nucleic Acids", Science 1992, 258, 1481-1485.
Helene, C. and Toulme, "Specific Regulation of Gene Expression by Antisense, Sense and Antigene Nucleic Acids", Biochimica et Biophysica Acta 1990, 1049, 99-125.
Huang, S. et al., "Acyclic nucleic acid analogues: Synthesis and oligomerization of .tau., 4-diamino-2-oxo-1 (2H) -pyrimidinepentanoic acid and, 4-diamino -2-oxo-1 (2H) -pyrimidinehexanoic acid", J. Org. Chem. 1991, 56, 6007-6018.
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. Commun. 1993, 518-519.
Hyrup, B. et al., "Structure-Activity Studies of the Binding of Modified Peptide Nucleic Acids (PNAs) to DNA", J. Am. Chem. Soc. 1994, 116, 7964-7970.
Kim, S. et al., "Right-Handed Triplex Formed between Peptide Nucleic Acid PNA-T.sub.8 and Poly(dA) Shown by Linear and Circular Dichroism Spectroscopy", J. Am. Chem. Soc. 1993, 115(15), 6477-6481.
Kosynkina, L. et al., "A Convenient Synthesis of Chiral Peptide Nucleic Acid (PNA) Monomers", Tetrahedron Letters 1994, 35(29), 5173-5176.
Inaki, Y. and Takemoto, "Functionality and Applicability of Synthetic Acid Analysis," Current Topics Polym. Sci 1987, 1, 80-100.
Inaki, Y., "Synthetic Nucleic Acid Analogs", Prog. Polym. Sci. 1992, 17, 515-570.
Lagriffoul, P. et al., "The Synthesis, Co-oligomerization and Hybridization of a Thymine-Thymine Heterodimer Containing PNA", Bioorganic & Medicinal Chemistry 1994, 4(8), 1081-1082.
Leijon, M. et al., "Structural Characterization of PNA-DNA Duplexes by NMR. Evidence for DNA in a B-like Conformation", Biochemistry 1994, 33, 9820-9825.
Lu et al., "Synthesis of Polyesters Containing Nucleic Acid Base Derivatives as Pending Side Chains," Journal of Polymer Science: Part A: Polymer Chemistry 1986, 24, 525-536.
Mack, D. et al., "Design and Chemical Synthesis of a Sequence-Specific DNA-Cleaving Protein", J. Am. Chem. Soc. 1988, 110, 7572-7574.
Mollegaard, N. et al., "Peptide Nucleic Acid DNA Strand Displacement Loops as Artificial Transcription Promoters", PNAS USA 1994, 91, 3892-3895.
Nagae, S. et al., "Functional Monomers and Polymers. CLIV. Application of Nucleic Acid Base Containing Polymers to High Performance Liquid Chromatography", Journal of Polymer Science: Part A: Polymer Chemistry 1989, 27, 2593-2609.
Nielsen, P. et al., "Peptide nucleic Acids (PNAs): Potential Antisense and Anti-Gene Agents", Anti-Cancer Drug Design 1993, 8, 53-63.
Nielsen, P., "Peptide Nucleic Acids (PNA): Potential Antiviral Agents", International Antiviral News 1993, 1(3), 37-39.
Nielsen, P. et al., Peptide Nucleic Acids (PNA): Oligonucleotide Analogs With a Polyamide Backbone, in "Antisense Research and Applications", S.T. Crooke and B. Lebleu (eds) CRC Press, Boca Raton, FL 1993.
Nielsen, P., Peptide Nucleic Acid (PNA). A DNA Mimic with a Peptide Backbone, Bioconjugate Chem. 1994, 5, 3-7.
Nielsen, P., "Peptide Nucleic Acid (PNA): A Model Structure for the Primordial Genetic Material", Origins of Life and Evolution of the Biosphere 1993, 23, 323-327.
Nielsen, P. et al., "Sequence-Specific Transcription Arrest by Peptide Nucleic Acid Bound to the DNA Template Strand", Gene 1994, 149, 139-145.
Nielsen, P.E., et al., "Sequence-Selective Recognition of DNA by Strand Displacement with a Thymine-Substituted Polyamide", Science 1991, 254, 1497-1500.
Nielsen, Peter E. et al., "Photochemical Cleavage or DNA by Nitrobenzamides Linked to 9-Aminoacridine" Biochem.1988 27, 6338-6343.
Nielsen, P. et al., "Sequence Specific Inhibition of DNA Restriction Enzyme Cleavage by PNA", Nucleic Acids Research 1993, 21(2), 197-200.
Matthews, J. and Kricka, "Analytical Strategies for the Use of DNA Probes", Analytical Biochemistry 1988, 169, 1-25.
Nollet, A.H.J. et al., "Unconventional Nucleotide Analogues--I N.sup.9 -Purinyl .alpha.-Amino Acids", Tetrahedron 1969, 25, 5971-5981.
Nollet, A.J.H. and Pandit, U.K., "Unconventional Nucleotide Analogues--II. Synthesis of the Adenyl Analogue of Willardiine", Tetrahedron 1969, 25, 5983-5987.
Nollet, A.J.H. and Pandit, "Unconventional Nucleotide Analogues--III. 4-(N.sup.1 -pyrimidyl)-2-Aminobutyric Acids", Tetrahedron 1968, 25, 5989-5994.
Nollet, A.J.H. and Pandit, U.K., "Michael Addition of 4-O-Ethyluracil. A Method for specific N.sub.1 -Alkylation of Hydroxypyrimidines", Tetrahedron Letters 1969, 53, 4605-4606.
Orum, H. et al, "Single Base Pair Mutation Analysis by PNA Directed PCR Clamping", Nucleic Acids Research 1993, 21(23), 5332-5336.
Parkanyi, C. et al., "Synthesis of Polymethylene Chainbridged 6-substituted 8-azapurines and Related Compounds", Collect. Czech. Chem. Commun. 1991, 56, 2382-2388.
Peffer, N. et al, "Strand-Invasion of Duplex DNA by Peptide Nucleic Acid Oligomers", PNAS USA 1993, 90, 10648-10652.
Pitha, P. et al., "Inhibition of murine leukemia virus replication by poly(vinyluracil) and poly(vinyladenine)", PNAS USA 1973, 70(4), 1204-1208.
Pitha, J., "Physiological activities of synthetic analogs of polynucleotides", Advances in Poly

Affiliated with

Also associated with

Rating

Chiral peptide nucleic acid monomers and oligomers does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Chiral peptide nucleic acid monomers and oligomers, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chiral peptide nucleic acid monomers and oligomers will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2136840