Non-enzymatic ligation of oligonucleotides

Details Non-enzymatic ligation of oligonucleotides Non-enzymatic ligation of oligonucleotides

1995-01-23

1995-12-19

Robinson, Douglas W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 2433, 536 245, C07H 100, C07H 2100

Patent

active

054769302

ABSTRACT:
A process for non-enzymatic convalent ligation of two oligonucleotides having the structure shown below: ##STR1## The spontaneous reaction of these above oligonucleotides produces a thiophosphorylacetylamino linkage as shown below: ##STR2## When carried out in the presence of a template, this reaction gives 90% yields within 20 minutes at micromolar concentrations.

REFERENCES:
patent: 5237016 (1993-08-01), Ghosh et al.
Bischofberger, N. and Wagner, R. W., Virology, 3:57-66 (1992) "Antisense approaches to antiviral agents".
Uhlmann, E. et al., Chemical Reviews, 90:543-584 (1990) "Antisense Oligonucleotides: A New Therapeutic Principle".
Proceedings, International Conference on Nucleic Acid Medical Applications, Cancun, Mexico (Jan. 26-30, 1993).
Proceedings, International Conference on Nucleic Acid Medical Applications, Cancun, Mexico, pp. 59-63 (Jan. 1993).
Woolf, C. M. et al., Proc. Natl. Acad. Sci. USA, 89:7305-7309 (1992) "Specificity of antisense oligonucleotides in vivo".
Naylor, R.; Gilham, P. T. Biochemistry, 5:2722-2728 (1966) "Studies on Some Interactions & Reactions of Oligonucleotides in Aqueous Solution".
Sokolova, N. I. et al., FEBS Letters, 232:153-155 (1988) "Chemical reactions within DNA duplexes".
Shabarova, Z. A. Biochimie, 70:1323-1334 (1988) "Chemical development in design of oligonucleotide probes for binding to DNA and RNA".
Kool, E. T., J. Am. Chem. Soc., 113:6265-6266 (1991) "Molecular Recognition by Circular Oligonucleotides: Increasing Selectivity of DNA Binding".
Ashley, G. W.; Kushlan, D. M. Biochemistry, 30:2927-2933 (1991) "Chemical Synthesis of Oligodeoxynucleotide Dumbbells".
Luebke, K. J. et al, J. Am. Chem. Soc., 113:7447-7448 (1991) "Nonenzymatic Sequence-Specific Ligation of Double-Helical DNA".
Luebke, K. J. et al., Nucleic Acids Res., 20:3005-3009 (1992) "Nonenzymatic ligation of double-helical DNA by alternate-strand triple helix formation".
Prakash, G.; Kool, E. T., J. Am. Chem. Soc., 114:3523-3527 (1992) "Structural Effects in Recognition of DNA by Circular Oligonucleotides".
Purmal, A. A. et al., Nucleic Acids Res., 20:3713-3719 (1992) "A new affinity reagent for site-spec., covalent attc. of DNA to active-site nucleophiles: appl. to EcoR1 and Rsrl . . . ".
Gryaznov, S. M.; Letsinger, R. L., J. Am. Chem. Soc., 115:3808-3809 (1993) "Chemical Ligation of Oligonucleotides in Presence and Absence of a Template".
Goodwin, J. T.; Lynn, D. G. J. Am. Chem. Soc., 114:9197-9198 (1992) "Template-Directed Synthesis: Use of a Reversible Reaction".
Gryaznov, S. M., Letsinger, R. L. Nucleic Acids Res., 20:3403-3409 (1992) "Syntheses & properties of oligonucleotides containing aminodeoxythymidine units".
Thuong, N. T. et al., Terrahedron Lett., 28:4157-4160 (1987) "Synthese et Reactivite D'Oligothymidylates Substitutes Par un Agent Intercalant et un Group Thiophosphate".
Francois, J-C. et al., Proc. Natl. Acad. Sci. USA, 86:9702-9706 (1989) "Seq.-specific recog. and cleavage of duplex DNA via triple-helix formation by oligonucleotides covalently . . . ".
Beukers, R. et al., Recueil., 77:729-732 (1958) "The Effect of Ultraviolet Light on Some Components of Nucleoic Acids".
Letsinger, R. L. et al., J. Am. Chem. Soc. 87:2945-2953 (1965) "Photoinduced Substitution. II. Substitute Effects in Nucleophilic Displacement on Substituted Nitrobenzenes".
Mag, M. et al., Nucleic Acids Res., 19:1437-1441 (1991) "Synthesis & selective cleavage of oligodeoxynucleotide cont. bridged internucleotide 5'-phosphorothioate linkage".
Letsinger, R. L. et al., Proc. Natl. Acad. Sci. USA, 86:6553-6556 (1989) "Cholesteryl-conjugated oligonucleotides: Synthesis, properties, & activ. as inhibitors of replication".
Alberts et al. Molecular Biology of the Cell. Garland Publishing, Inc. New York 1983, p. 187.

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