Synthesis of oligonucleotide arrays using photocleavable protect

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

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536 2531, 536 2532, 536 2533, 536 2534, 536 256, 536124, 435 6, 435 792, 435 794, 435 795, 436518, 436527, 436528, 436807, C07H 2100

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060229632

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(R.sub.1)(R.sub.2)--O--C(O)-- wherein:

REFERENCES:
patent: 5143854 (1992-09-01), Pirrung et al.
patent: 5200051 (1993-04-01), Cozzette et al.
patent: 5353186 (1994-10-01), Fodor et al.
patent: 5384261 (1995-01-01), Winkler et al.
patent: 5424186 (1995-06-01), Fodor et al.
patent: 5430136 (1995-07-01), Ureda et al.
patent: 5445934 (1995-08-01), Fodor et al.
patent: 5489678 (1996-02-01), Fodor et al.
patent: 5639603 (1997-06-01), Dower et al.
patent: 5677195 (1997-10-01), Winkler et al.
patent: 5700637 (1997-12-01), Southern
Bos et al., "Amino-acid substitutions at codon 13 of the N-ras oncogene in human acute myeloid leukaemia" Nature 315:726-730 (1985).
Hochgeschwender et al., "Preferential expression of a defined T-cell receptor .beta.-chain gene in hapten-specific cytotoxic T-cell clones" Nature 322:376-378 (1986).
Verlaan-de Vries et al., "A dot-blot screening procedure for mutated ras oncogenes using synthetic oligodeoxynucleotides" Gene 50:313-320 (1986).
Elder, J.K., "Analysis of DNA Oligonucleotide Hybridization Data by Maximum Entropy" Maximum Entropy and Bayesian Methods, Proc. 12th Intl. Workshop, Paris, France, pp. 363-371 (1993).
Geysen et al., "Strategies for epitope analysis using peptide synthesis" J. Immunol. Meth. 102:259-274 (1987).
Houghten et al., "Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery" Nature 354:84-86 (1991).
Lam et al., "A new type of synthetic peptide library for identifying ligand-binding activity" Nature 354:82-84 (1991).
Southern et al., "Analyzing and Comparing Nucleic Acid Sequences by Hybridization to Arrays of Oligonucleotides: Evaluation Using Experimental Models" Genomics 13:1008-1017 (1992).
Fodor et al., "Light-Directed, Spatially Addressable Parallel Chemical Synthesis," Science, 251, 767-778 (1991).
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), 5157-5160 (1987).
Furuta et al., "New Photochemically Labile Protecting Group for Phosphates," Chemistry Letters, 1179-1182 (1993).
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, 3139-3142 (1993).
Givens et al., "Photochemistry of Phosphate Esters," Chem. Rev., 93, 55-66 (1993).
Iwamura et al., "1-(.alpha.-Diazobenzyl)pyrene: A Reagent for Photolabile and Fluorescent Protection of Carboxyl Groups of Amino Acids and Peptides," SYNLETT, 35-36 (1991).
Iwamura et al., "1-Pyrenylmethyl Esters, Photolabile Protecting Groups for Carboxylic Acids," Tetrahedron Letters, 28(6), 679-682 (1987).
Iwamura et al., "Photoreactivity of 1-Pyrenylmethyl Esters. Dependence on the Structure of the Carboxylic Acid Moieties and the Nature of the Excited States," Chemistry Letters, 1729-1732 (1987).
Okada et al., "(1-Pyrenyl)methyl Carbamates for Fluorescent "Caged" Amino Acids and Peptides," Photochemistry and Photobiology, 61(5), 431-434 (1995).
Pease et al., "Light-generated oligonucleotide arrays for rapid DNA sequence analysis," Proc. Natl. Acad. Sci. USA, 91, 5022-5026 (1994).
Holmes et al., "Development of a new photo-removable protecting group for the amino and carboxyl groups of amino acids" Peptides: Chemistry, Structure and Biology (Proceedings of the 13th American Peptide Symposium), 110-112 (1994).
Yankee et al., "Photosensitive Protecting Groups", Journal of the American Chemical Society, 92(21), 6333-6335 (1970).
Gordon et al., "Applications of Combinatorial Technologies to Drug Discovery. 2. Combinatorial Organic Synthesis , Library Screening Strategies, and Future Directions", Journal of Medicinal Chemistry, 37/10, 1385-1401 (1994).
Gallop et al., "Applications of Combinatorial Technologies to Drug Discovery. 1. Background and Peptide Combinatorial Libraries", Journal of Medicinal Chemistry, 37/9, 1233-1251, (1994).
Ajayaghosh et al., "Polymer-Supported Synthesis of Protected Peptide Segments on a Photosensitive O-Nitro (.alpha.-Methyl)Bromobenzyl Resin", Tetrahedron, 44/21, 6661-6666 (1988).
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, 31-45 (1990).
Williams et al., "Convergent Solid-Phase Peptide Synthesis", Tetrahedron, 49/48, 11065-11133 (1993).
Rich et al., "Preparation of a New 0-Nitrobenzyl Resin for Solid-Phase Synthesis of tert-Butyloxycarbonyl-Protected Peptide Acids", Journal of the American Chemical Society, 97(6), 1575-3261 (1974).
Wang et al., "Solid Phase Synthesis of Protected Peptides via Photolytic Cleavage of the .alpha.-Methylphenacy Ester Anchoring Linkage", J. Org. Chem, 41/20, 3258-3261 (1976).

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