Photolabile esters and their uses

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

10481707

ABSTRACT:
Compounds which are capable of generating acid on photolysis are disclosed, and the uses of these compounds, especially for deprotecting the termini of nucleic acid molecules or peptides during synthesis of arrays. The compounds described herein may be employed in the detritylation of 5′-O-dimethoxytrityl (DMT) protected nucleotides by photolysing the compounds to generate an acid capable of removing the DMT group allowing oligonucleotide arrays to be synthesised using readily available 5′-O-DMT-nucleoside-3′-O-phosphoramidite monomers conventionally used in solid phase nucleic acid synthesis. A method of avoiding the effects of stray light in projection lithography techniques is also disclosed.

REFERENCES:
patent: 22 07 574 (1973-08-01), None
patent: 0 046 028 (1982-02-01), None
patent: 0 046 083 (1982-02-01), None
patent: 0 077 961 (1983-05-01), None
patent: 0 476 865 (1992-03-01), None
patent: 2001 190143 (2001-04-01), None
patent: WO 99/41007 (1999-08-01), None
patent: WO 00/66259 (2000-11-01), None
patent: WO 01/32720 (2001-05-01), None
Hiroyoshi Kamogawa, Seichu Nin and Manabu Horiuchi Polymers of 4-vinyl-2′-nitrodiphenylmethyl carboxylates capable of releasing functional acid by light Reactive Polymers, 18 (1992) 125-131.
Hiroyoshi Kamogawa, Seichu Nin and Manabu Horiuchi Reactive Polymers, 18 (1992) 125-131.
Kamogawa, H., et al., “Polymers of 4-vinyl-2′-nitrodiphenylmethyl carboxylates capable of releasing functional acid by light,” Reactive Polymers, 18:125-131, (1992).
Houlihan, F.M., “The Photo and Thermo Chemistry of Select 2,6-Dinitrobenzyl Esters in Polymer Matrices: Studies Pertaining to Chemical Amplification and Imaging”, vol. 61: 296-301 (1989).
Gao, et al. “Oligonucleotide Synthesis Using Solution Photogenerated Acids”, J. Am. Chem. Soc. vol. 120: 12698-12699 (1998).
Gao, X., et al., “A flexible light-directed DNA chip synthesis gated by deprotection using solution photogenerated acids”, vol. 29(22): 4744-4750 (2001).
Koshi, K., et al., “The Synthesis of 2,3-Dimethoxy-5-methyl-p-benzoquinone and Related Compounds”, Chem. Pharm. Bull. 16(12): 2343-2350 (1968).
Cunico, R.F., “Aminooxycarbene behavior of a carbamoylsilane”, Tetrahedron Letters, 42: 2931-2932 (2001).
Corrie, J.E.T., et al., Synthesis and Absolute Stereochemistry of the Two Disastereoisomers ofP3-1-(2-Nitrophenyl)ethyl Adenosine Triphosphate (‘Caged’ ATP), J. Chem. Soc. Perkin Trans. 1: 1015-1019 (1992).
Seebach, D., et al., “Entantioselective addition of Aryl Groups to Aromatic Aldehydes Using Chiral Aryltitanium Binaphtol Derivatives”, Chem. Ber. 118: 3673-3682 (1985); See English Abstract.
Puckowski, R.T., et al., “The Preparation and Reactions of Some Optically Active Substituted Benzhydrols”, J. Chem. Soc. 3555-3564 (1959).
Batey, R.A., et al., “Potassium Alkenyl- and Aryltrifluoroborates: Stable and Efficient Agents for Rhodium-Catalyzed Addition to Aldehydes and Enones”, Organic Letters 1(10): 1683-1686 (1999).
Miyashita, K., et al., “Novel indole-ring formation by thermolysis of 2-(N-acylamino)- benzylphosphonium salts. Effective synthesis of 2-trifluoromethyl-indoles”, J. Chem., Soc., Perkin Trans., 1: 1261-1268 (1996).
Effenberger, F., et al., Hydroxyalkylation, Acylation, Formylation, and Carboxylation of 2-Nitro- and 2-Chloro-1-(trimethylsily)benzene. Chem. Ber. 118: 3900-3914 (1985); See English Abstract.
Smirnov, S.K., et al., “4,5-Dimethoxy-2-nitrobenzhydrol” Molecules 4: M113 (1999).
Waksmundzka-Hajnos, M., “Chromatographic separation of nitro-phenones and their reduced derivatives on thin layers of polar adsorbents”, Acta Chromatographica No. 7 p. 159-171 (1997).
Walser, A., et al., “A cinnonline 2-oxide from 2-nitrosobenzophenone”, J. Heterocyclic Chem., 13(4): 907-908 (1976).
Barzynski, H., et al., “Zur Photolyse von makromolekularen o-Nitrobenzylderivaten” Die Angewandte Makromolekulare Chemie 93: 131-141 (1981); See English Abstract.
Colominas, C., et al., “Conformational folding induced by II-II interaction in a series of flexible dyads consisting of isomeric mesoporphyrin nitrobenzyl esters”, J. Chem. Soc. Perkin Trans., 2: 997-1004 (1996).
Yip, R.W., et al., “Photochemistry of the o-Nitrobenzyl System in Solution: Evidence for Singlet State Intramolecular Hydrogen Abstraction”, J. Phys. Chem., 89: 5328-5330 (1985).
Reichmanis, E., et al., “o-Nitrobenzyl Photochemistry: Solution vs. Solid-State Behavior”, J. Of Polymer Science 23: 1-8 (1985).
Wharton, C.W., et al., “Use of Caged Compounds in Studies of Bioelectronic Imaging and Pattern Recognition”, Methods in Enzymology, vol. 291: 245-250, G. Marriott editor of “Caged Compounds” (1998).
Paul, C.H., et al., “Acid binding and detritylation during oligonucleotide synthesis”, Nucleic Acid Research, vol. 24: 3048-3052 (1996).
Cummings, R.T., et al., “Photoactivable fluorophores. 1. Synthesis and photoactivation of o-Nitrobenzyl-quenched fluorescent carbamates.” Tetrahedron Letters, vol. 29: 65-68 (1988).
Walker, J.W., et al., “Photolabile 1-(2-Nitrophenyl)ethyl Phosphate Esters of Adenine Nucleotide Analogues. Synthesis and Mechanism of Photolysis”, J. Am. Chem. Soc. vol. 110: 7170-7177 (1988).
Kim, S., et al., “Intramolecular Nucleophilic Participation. VIII. Acetolysis of o- and ρ-Nitro- and o and ρ-Carbophenoxybenzhydryl Bromides” J. Am. Chem. Soc. vol. 92: p. 5452-5456 (1970).
Cocker, W., et al., “A Preparation of m-Dimethylaminobenzaldehyde”, J. Chem. Soc., p. 751-753 (1938).
LeProust, E., et al., “Digital Light-Directed Synthesis. A Microarray Platform That Permits Rapid Reaction Optimization on a Combinatorial Basis”, J. Comb. Chem., vol. 2: 349-354 (2000).
Pease, A.C., et al., “Light-generated oligonucleotide arrays for rapid DNA sequence analysis”, Proc. Natl. Acad. Sci. USA, vol. 91: 5022-5026 (1994).
McGall, G.H., et al., “High-Density Oligonucleotide Probe Arrays”, Advances in Nucleic Acid and Protein Analyses, Manipulation, and Sequencing, Editors: P.A. Limbach, et al., Proceedings of SPIE vol. 3926: 1017-2661 (2000).
Beecher, J.E., et al., “Chemically Amplified Photolithography for the Fabrication of High Density Oligonucleotide Arrays”, Polymeric Materials Sci. Eng. (Washington) 76, p. 597-598 (1997).
Eckstein, F., Editor, “Oligonucleotides and Analogues: a practical approach”, IRL Press Ltd., Oxford, NY, Tokyo, p. vii, xxiii-xxiv, 1-24 (1991).
Caruthers, M.H., “Chemical Synthesis of DNA and DNA Analogues”, Acc. Chem. Res., 24: 278-284 (1991).
Beaucage, S.L., et al., “Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach”, Tetrahedron vol. 48: p. 2223-2311 (1992).
Fodor, S.P.A., et al., “Light-Directed, Spatially Addressable Parallel Chemical Synthesis”, Science vol. 251: p. 767-773 (1991).
Singh-Gasson, S., et al., “Maskless fabrication of light-directed oligonucleotide microarrays using a digital micromirror array”, Nature Biotech., vol. 17, p. 947-978 (1999).
Garner, H.R., Abstracts of Cambridge Healthtech Institute Conference “Lab Chips and Microarrays for Biotechnological Applications”, Zurich, Jan. 13-15, 1999.
Stähler, P.F., Abstract of IBC Conference “Chips to Hits”, Philadelphia, Nov. 6-9, 2000.
Hornbeck, L.J., “From cathode rays to digital micromirrors: A history of electronic projection display technology”, Texas Instruments Technical Journal, vol. 15 July-Sept. p. 7-46 (1998) (Obtainable at www.ti.com/dlp).
Bevington, “Chapter Three: Distributions” from “Data Reduction and Error Analysis for the Physical Sciences”, p. 27-37 McGraw-Hill Book Comany, NY (1969).
Temsamani, J., et al., “

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Photolabile esters and their uses does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Photolabile esters and their uses, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photolabile esters and their uses will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3883532

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.