Chemistry of hydrocarbon compounds – Special chemical considerations – Process including synthesis of nonhydrocarbon intermediate
Reexamination Certificate
2006-08-22
2006-08-22
Wilson, James O. (Department: 1623)
Chemistry of hydrocarbon compounds
Special chemical considerations
Process including synthesis of nonhydrocarbon intermediate
C585S932000, C585S933000, C585S934000, C585S935000, C585S400000, C585S800000
Reexamination Certificate
active
07094943
ABSTRACT:
Multifunctional liquid phase carriers (LPCs) and methods of using LPCs for the preparation of biopolymers are provided. The LPCs are highly symmetrical compounds that possess more than two points of attachment for biopolymer synthesis. The LPCs have the formula Sp(X1)n, where Sp is a highly symmetrical moiety such that all X1groups are equivalent. X1is a functional group that is suitable for biopolymer synthesis, including OH, SH, NH2, COOH and the like. Biopolymers that may be produced using the methods provided include oligonucleotides, peptides, protein nucleic acids (PNAs) and oligosaccharides. Analogs of the biopolymers may also be prepared using the methods.
REFERENCES:
patent: 4749742 (1988-06-01), Elmore
patent: 4794150 (1988-12-01), Steel
patent: 5037882 (1991-08-01), Steel
patent: 5077210 (1991-12-01), Eigler et al.
patent: 5198540 (1993-03-01), Koster
patent: 5221736 (1993-06-01), Coolidge et al.
patent: 5246840 (1993-09-01), Nilsson
patent: 5262331 (1993-11-01), Salisbury et al.
patent: 5288637 (1994-02-01), Roth
patent: 5374655 (1994-12-01), Kashem et al.
patent: 5492821 (1996-02-01), Callstrom et al.
patent: 5532147 (1996-07-01), Nilsson
patent: 5539083 (1996-07-01), Cook et al.
patent: 5547835 (1996-08-01), Koster
patent: 5552471 (1996-09-01), Woo et al.
patent: 5552535 (1996-09-01), McLean et al.
patent: 5571902 (1996-11-01), Ravikumar et al.
patent: 5583042 (1996-12-01), Roth
patent: 5610289 (1997-03-01), Cook et al.
patent: 5616698 (1997-04-01), Krepinsky et al.
patent: 5616700 (1997-04-01), Reddy et al.
patent: 5635488 (1997-06-01), Cook et al.
patent: 5635598 (1997-06-01), Lebl et al.
patent: 5637719 (1997-06-01), Carpino et al.
patent: 5639633 (1997-06-01), Callstrom et al.
patent: 5641862 (1997-06-01), Rutter et al.
patent: 5644029 (1997-07-01), Carpino
patent: 5648462 (1997-07-01), Funakoshi et al.
patent: 5648480 (1997-07-01), Letsinger et al.
patent: 5652358 (1997-07-01), Pfleiderer et al.
patent: 5668266 (1997-09-01), Ruth
patent: 5679773 (1997-10-01), Holmes
patent: 5700922 (1997-12-01), Cook
patent: 5705333 (1998-01-01), Shah et al.
patent: 5705621 (1998-01-01), Ravikumar
patent: 5714331 (1998-02-01), Buchardt et al.
patent: 5719262 (1998-02-01), Buchardt et al.
patent: 5726243 (1998-03-01), Fields
patent: 5736336 (1998-04-01), Buchardt et al.
patent: 5736625 (1998-04-01), Callstrom et al.
patent: 5736626 (1998-04-01), Mullah et al.
patent: 6001966 (1999-12-01), Pieken et al.
patent: 0642798 (1995-03-01), None
patent: 8401779 (1984-05-01), None
patent: 8912624 (1989-12-01), None
patent: 9210092 (1992-06-01), None
patent: 9603148 (1996-02-01), None
patent: 9714706 (1997-04-01), None
patent: 9820166 (1998-05-01), None
patent: 9910362 (1999-03-01), None
International Search Report, PCT/US 99/08939, Apr. 26, 1999.
Konig, B., et al., Tetrahedron Letters, 39(16):2307-2310 (1998).
Ritzen, A., et al., Tetrahedron: Asymmetry, 9(19):3491-3496 (1998).
Shchepinov et al., Nucleic Acid Research, 25(22):4447-4454 (1997).
Shinozuka, K. et al., Journal of the Chemical Society, Chemical Communications, 11:1377-1378 (1994).
Tuchscherer, G., et al., Journal of Biotechnology, 41(2):197-210 (1995).
Backes, B.J. et al., “Activation Method to Prepare a Highly Reactive Acylsulfonamide “Safety Catch” Linker for Solid-Phase Synthesis1”,J. Am. Chem. Soc., 118:3055-3056 (1996).
Batista-Viera, F. et al., “A New Method for Reversible Immobilization of Thiol Biomolecules Based on Solid-Phase Bound Thiolsulfonate Groups”,Appl. Biochem. Biotech., 31:175-195 (1991).
Beaucage, S.L. and Caruthers, M.H., “Deoxynucleoside Phosphoramidites—A New Class of Key Intermediates for Deoxypolynucleotide Synthesis”,Tetrahedron Lett., 22(20):1859-1862 (1981).
Beaucage, S.L. and Iyer, R.P., “Advances on the Synthesis of Oligonucleotides by the Phosphoramidite Approach”,Tetrahedron, 48(12):2223-2311 (1992).
Beaucage, S.L. and Iyer, R.P., “The Functionalization of Oligonucleotides via Phosphoramidite Derivatives”,Tetrahedron, 49(10):1925-1963 (1993).
Beaucage, S.L. and Iyer, R.P., “The Synthesis of Modified Oligonucleotides by the Phosphoramidite Approach and Their Applications”,Tetrahedron, 49(28):6123-6194 (1993).
Beck, S. and Koster, H., “Applications of Dioxetane Chemiluminescent Probes to Molecular Biology”,Anal. Chem., 62:2258-2270 (1990).
Bhargava, K.K. et al., “Synthesis of a Cyclic Analogue of Oxidized Glutathione by an Intersite Reaction in a Swollen Polymer Network”,J. Am. Chem. Soc., 105:3247-3251 (1983).
Biernat, J. et al., “Purification Orientated Synthesis of Oligodeoxynucleotides in Solution”,Tetrahedron Lett., 24(8):751-754 (1983).
Bray, A.M. et al., “Direct Cleavage of Peptides from a Solid Support into Aqueous Buffer. Application in Simultaneous Multiple Peptide Synthesis”,J. Org. Chem., 56:6659-6666 (1991).
Brown, B.B. et al., “A single-bead decode strategy using electrospray ionization mass spectrometry and a new photolabile linker: 3-amino-3-(2-nitrophenyl)propionic acid”,Mol. Divers., 1:4-12 (1995).
Brown, E.L. et al., “Chemical Synthesis and Cloning of a Tyrosine tRNA Gene”,Meth. Enzymol., 68:109-151 (1979).
Brown, S.C. et al., “NMR Solution Structure of a Peptide Nucleic Acid Complexed with RNA”,Science, 265:777-780 (1994).
Burgess, K. et al., “An Approach to Photolabile, Fluorescent Protecting Groups”,J. Org. Chem., 62:5165-5168 (1997).
Cardno, M. and Bradley, M., “A Simple Multiple Release System for Combinatorial Library and Peptide Analysis”,Tetrahedron Lett., 37(1):135-138 (1996).
Chan, W.C. and Mellor, S.L., “Reductive Alkylation of 9-Amino-xanthen-3-yloxymethylpoly(styrene): a Novel Procedure for the Synthesis of Peptidyl N-Alkyl Amides by Fmoc/ButChemistry”,J. Chem. Soc. Chem. Commun., 1475-1476 (1995).
Cusack, N.J. et al., “Block Synthesis of Oligonucleotides by the Phosphotriester Approach”,Tetrahedron Lett., 24:2209-2212 (1973).
DeGrado, W.F. and Kaiser, E.T., “Polymer-Bound Oxime Esters as Supports for Solid-Phase Peptide Synthesis. Preparation of Protected Peptide Fragments”,J. Org. Chem., 45:1295-1300 (1980).
Eckstein, F., ed., “Oligonucleotides and Analogues : A Practical Approach”, pp. 49-51; 58-59; 137-139; 255-259, IRL Press, Oxford, 1991.
Entwistle, I.D., “The Use of 2-N-Nitrophenylpropionic Acid as a Protecting Group for Amino and Hydroxyl Functions to be Recovered by Hydrogen Transfer Reduction”,Tetrahedron Lett., 6:555-558 (1979).
Fattom, A. et al., “Comparative Immunogenicity of Conjugates Composed of theStaphylococcus aureusType 8 Capsular Polysaccharide Bound to Carrier Proteins by Adipic Acid Dihydrazide or N-Succinimidyl-3-(2-Pyridyldithio)propionate”,Infection and Immun., 60(2):584-589 (1992).
Frechet, J.M.J. and Nuyens, L.J., “Use of Polymers as Protecting Groups in Organic Synthesis. III. Selective Functionalization of Polyhydroxy Alcohols”,Can. J. Chem., 54:926-934 (1976).
Froehler, B.C., “Deoxynucleoside H-Phosphonate Diester Intermediates in the Synthesis of Internucleotide Phosphate Analogues”,Tetrahedron Lett., 27(46):5575-5578 (1986).
Froehler, B.C. and Matteucci, M.D., “Nucleoside H-Phosphonates: Valuable Intermediates in the Synthesis of Deoxyoligonucleotides”,Tetrahedron Lett., 27(4):469-472 (1986).
Froehler, B.C. and Matteucci, M.D., “Substituted 5-Phenyltetrazoles: Improved Activators of Deoxynucleoside Phosphoramidites in Deoxyoligonucleotide Synthesis”,Tetrahedron Lett., 24(31):3171-3174 (1983).
Gait, M.J., ed., “Oligonucleotide Synthesis : A Practical Approach”, IRL Practical Approach Series, IRL Press, Oxford, 1984.
Garegg, P.J. et al., “Nucleoside H-Phosphonates. III. Chemical Synthesis of Oligodeoxyribonucleotides by the Hydrogenphosphonate Approach”,Tetrahedron Lett., 27(34):4051-4054 (1986).
Gayo, L.M. and Suto, M.J., “Traceless
Köster Hubert
Wörl Ralf
Fish & Richardson P.C.
Köster Hubert
Seidman Stephanie
Ward Paul V.
Wilson James O.
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