Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2005-04-19
2005-04-19
Wilson, James (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S124000, C536S025310, C536S025320, C536S025330, C536S025340, C436S518000, C514S019300, C514S275000, C514S278000, C435S006120, C435S007920, C435S007940
Reexamination Certificate
active
06881836
ABSTRACT:
Novel compounds are provided which are useful as linking groups in chemical synthesis, preferably in the solid phase synthesis of oligonucleotides and polypeptides. These compounds are generally photolabile and comprise protecting groups which can be removed by photolysis to unmask a reactive group. The protecting group has the general formula Ar—C(R1)(R2)—O—C(O)— wherein:Ar is an optionally substituted fused polycyclic aryl or heteroaromatic group or a vinylogous derivative thereof;R1and R2 are independently H, optionally substituted alkyl, alkenyl or alkynyl, optionally substituted aryl or optionally substituted heteroaromatic, or a vinylogous derivative of the foregoing; andX is a leaving group, a chemical fragment linked to Ar—C(R1)(R2)—O—C(O)— via a heteroatom, or a solid support; provided that when Ar is 1-pyrenyl and R1and R2are H, X is not linked to Ar—C(R1)(R2)—O—C(O)— via a nitrogen atom. Preferred embodiments are those in which Ar is a fused polycyclic aromatic hydrocarbon and in which the substituents on Ar, R1and R2are electron donating groups. A particularly preferred protecting group is the “PYMOC” protecting group, pyrenylmethyloxycarbonyl, where Ar is pyrenyl and R1and R2are H.Also provided is a method of forming, from component molecules, a plurality of compounds on a support, each compound occupying a separate predefined region of the support, using the protected compounds described above.
REFERENCES:
patent: 4242974 (1981-01-01), Beckerman
patent: 5143854 (1992-09-01), Pirrung et al.
patent: 5200051 (1993-04-01), Cozzette et al.
patent: 5212050 (1993-05-01), Mier et al.
patent: 5215899 (1993-06-01), Dattagupta
patent: 5242974 (1993-09-01), Holmes
patent: 5384261 (1995-01-01), Winkler et al.
patent: 5412087 (1995-05-01), McGall et al.
patent: 5413854 (1995-05-01), Sato
patent: 5420328 (1995-05-01), Campbell
patent: 5424186 (1995-06-01), Fodor et al.
patent: 5430136 (1995-07-01), Urdea et al.
patent: 5445934 (1995-08-01), Fodor et al.
patent: 5489678 (1996-02-01), Fodor et al.
patent: 5503805 (1996-04-01), Sugarman et al.
patent: 5541061 (1996-07-01), Fodor et al.
patent: 5580697 (1996-12-01), Keana et al.
patent: 5582955 (1996-12-01), Keana et al.
patent: 5639603 (1997-06-01), Dower et al.
patent: 5677195 (1997-10-01), Winkler et al.
patent: 5700637 (1997-12-01), Southern
patent: 5770358 (1998-06-01), Dower et al.
patent: 5830539 (1998-11-01), Yan et al.
patent: 5959098 (1999-09-01), Goldberg et al.
patent: 6022597 (2000-02-01), Yan et al.
patent: 6022963 (2000-02-01), McGall et al.
patent: 6054504 (2000-04-01), Dalla Riva Toma
patent: 6147205 (2000-11-01), McGall et al.
patent: WO-8910977 (1989-11-01), None
patent: WO-9015070 (1990-12-01), None
patent: WO-9210092 (1992-06-01), None
patent: WO-9212492 (1992-07-01), None
patent: WO-9306121 (1993-04-01), None
Adams, S..R. ,et al. ,“Controlling cell chemistry with caged compounds”,Ann. Rev. Physiol., 55, (1993),pp. 755-784.
Ajayaghosh,et al. ,“Polymer-supported synthesis of protected peptide segments on a photosensitive o-nitro (alpha-methyl) bromobenzyl resin”,Tetrahedron Letters, 44 (21), (1988),pp. 6661-6666.
Amit, B..,et al. ,“Photosensitive protecting groups of amino sugars and their use in glycoside synthesis. 2-nitrobenzyloxycarbonylamino and 6-nitroveratryloxycarbonylamino derivatives”,J. Org. Chem., 39, (1974),pp. 192-196.
Atherton, E..,“Table of Contents”,Solid Phase Peptide Synthesis: A Practical Approach, New York: IRL Press at Oxford University Press,(1989),pp. vii-ix.
Bos,et al. ,“Amino-acid substitutions at condon 13 of the N-ras oncogene in human acute myeloid leukamia”,Nature, 315, (1985),pp. 726-730.
Corrie, J..E. ,et al. ,“Chapter 5: Caged Nucleotides and Neurotransmitters”,In: Biological Applications of Photochemical Switches, vol. 2(Bioorganic Photochemistry Series), Morrison, H. Ed., J. Wiley & Sons,(1993),pp. 243-305.
Crooke, S..T. ,et al. ,“Table of Contents”,Antisense Research and Applications, Crooke, S.T , et al., Ed., CRC Press, Boca Raton, FL,(1993),4 pages.
Elder, J..K. ,“Analysis of DNA oligonucleotide hybridization data by maximum entropy”,In: Maximum Entropy and Bayesian Methods—Proceedings of the Twelfth International Workshop, Mohammad-Dhafari and Demoment, G., Eds., Kluwer Academic Publishers, Paris, France,(1993),pp. 363-371.
Fodor,et al. ,“Light-directed, spatialyl addressable parallel chemical synthesis”,Science, 251, (1991),pp. 767-773.
Fourrey,et al. ,“1,1-bis-(4-methoxyphenyl)-1′-pyrenyl methyl (bmpm): A New Fluorescent 5′ Protecting Group for the Purification of Unmodified and Modified Oligonucleotides”,Tetrahedron Letters, 28(43), (1987),pp. 5157-5160.
Furuta,et al. ,“Direct Esterification of Phosphates with Various Halides and Its Application to Synthesis of cAMP Alkyl Triesters”,J. Chem Soc. Perkin Trans., 1, (1993),pp. 3139-3142.
Furuta,et al. ,“New Photochemically Labile Protecting Group for Phosphates”,Chemistry Letters, (1993),pp. 1179-1182.
Gallop,et al. ,“Applications of Combinatorial Technologies to Drug Delivery. 1. Background and Peptide Combinatorial Libraries”,J. Med. Chem., 37 (9), (1994),pp. 1233-1251.
Geysen,et al. ,“Strategies for Epitope Analysis Using Peptide Synthesis”,J. Immunol. Meth., 102, (1987),pp. 259-274.
Givens, R..S. ,et al. ,“Photochemistry of Phosphates Esters”,Chem. Rev., 93, (1993),pp. 55-66.
Gordon,et al. ,“Applications of Combinatorial Technologies to Drug Discovery. 2. Combinatorial Organic Synthesis, Library Screening Strategies, and Future Directions”,J. Med. Chem., 37(10), (1994),pp. 1385-1401.
Hammer,et al. ,“Practical Approach to Solid-Phase Synthesis of c-terminal Peptide Amides Under Mild Conditions Based on a Photolysable Anchoring Linkage”,Int. J. Peptide Protein Res., 36, (1990),pp. 31-45.
Hochgeschwender,et al. ,“Preferential Expression of a Defined T-cell Receptor Beta-chain gene in Hapten-specific Cytotoxic T-cell Clones”,Nature, 322, (1986),pp. 376-378.
Holmes,et al. ,“Development of a New Photo-removable Protecting Group for the Amino and Carboxyl Groups of Amino Acids”,In: Peptides: Chemistry, Structure, and Biology, vol. 13, Hodges, R.S., et al., Eds., Escom Science Publishers (Proceeding of the 13th American Peptide Symposium: Jun. 20-25, 1993, Edmonton, Alberta, Canada),(1994),pp. 110-112.
Houghten,et al. ,“Generation and use of synthetic peptide combinatorial libraries for basic research and drug delivery”,Nature, 354, (1991),pp. 84-86.
Iwamura,et al. ,“1-(alpha-diazbenzyl) pyrene: a reagent for photolabile and fluorescent protection of carboxyl groups of amino acids and peptides”,Synlett, (1991),pp. 35-36.
Iwamura,et al. ,“1-pyrenylmethyl esters, photolabile protecting groups for carboxylic acids”,Tetrahedron Letters, 28(6), (1987),pp. 679-682.
Iwamura,et al. ,“Photoreactivity of 1-pyrenylmethy esters. Dependence on the structure of the carboxylic acid moieties and the nature of the excited states”,Chemistry Letters, (1987),pp. 1729-1732.
Lam,“A new type of synthetic peptide library for identifying ligand-binding activity”,Nature, 354, (1991),pp. 82-84.
Lloyd-Williams,et al. ,“Convergent solid-phase peptide synthesis”,Tetrahedron Letters, 49(48), (1993),pp. 11065-11133.
McGall, G..H. ,“Chapter 2: The fabrication of high density oligonucleotides arrays for hybridization-based sequence analysis”,In: Biochip Arrays and Integrated Devices for Clinical Diagnostics, IBC Library Series, Based on the edited and updated transcripts from IBC's International Conference held in San Diego, CA,(Mar. 5-6, 1997),pp. 2.1-2.33.
Okada, S..,et al. ,“(1-pyrenyl)methyl carbamates for fluorescent “caged” amino acids and peptidesȁ
McGall Glenn H.
Nam Ngo Q.
Rava Richard P.
Affymetrix Inc
Khare Devesh
Malone Thomas E.
McGarrigle Philip L.
Schwegman, Lundberg, Woessner & kluth, P.A.
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