Incorporation of an aldehyde function in oligonucleotides

Bioconjugate Chemistry

Volumn 12, Issue 3, 2001, Pages 451-457

  Tilquin, Jean Marc ^a   Dechamps, Michel ^a   Sonveaux, Etienne ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; BIOCONJUGATE; FLUORIDE; NUCLEIC ACIDS, NUCLEIC ACID COMPONENTS AND THEIR DERIVATIVES; NUCLEOTIDE LIKE PHOSPHORAMIDITE; OLIGONUCLEOTIDE; OXIDATION; PERIODATE SODIUM; SYNTHESIS;

FLUORINE COMPOUNDS; SODIUM COMPOUNDS; STYRENE;

AUTOMATIC SYNTHESIS; BUILDING BLOCKES; DEPROTECTION; NUCLEIC BASE; O-CHAIN; PHOSPHORAMIDITES; SYNTHESISED; SYNTHONS; TERT-BUTYLDIMETHYLSILYL;

OLIGONUCLEOTIDES;

EID: 0035019368     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc000060u     Document Type: Article

References (44)

1. Agrawal, S., Christodoulou, C., and Gait, M. J. (1986) Efficient Methods for Attaching Nonradioactive Labels to the 5′ Ends of Synthetic Oligodeoxyribonucleotides. Nucleic Acids Res. 14, 6227-6245.
2. Aubert, Y., Bourgerie, S., Meunier, L., Mayer, R., Roche, A.-C., Monsigny, M., Thuong, N. T., and Asseline, U. (2000) Optimized Synthesis of Phosphorothioate Oligodeoxyribonucleotides Substituted with a 5′-Protected Thiol Function and a 3′-Amino Group. Nucleic Acids Res. 28, 818-825.
3. Bayard, B., Bisbal, C., Silhol, M., Cnockaert, J., Huez, G., and Lebleu, B. (1984) Increased Stability and Antiviral Activity of 2′-O-Phoshoglyceryl Derivatives of (2′-5′)oligo-(adenylate). Roles of Phosphodiesterases and Phosphatases in (2′-5′)Oligo(adenylate) Catabolism. Eur. J. Biochem. 142, 291-298.
4. Bentley, M. D., Roberts, M. J., and Harris, J. M. (1998) Reductive Amination Using Poly(ethylene glycol) Acetaldehyde Hydrate Generated in Situ: Applications to Chitosan and Lysozyme. J. Pharm. Sci. 87, 1446-1449.
5. Bongartz, J.-P., Aubertin, A.-M., Milhaud, P. G., and Lebleu, B. (1994) Improved Biological Activity of Antisense Oligonucleotides Conjugated to a Fusogenic Peptide. Nucleic Acids Res. 22, 4681-4688.
6. Bucala, R., Model, P., and Cerami, A. (1984) Modification of DNA by Reducing Sugars: A Possible Mechanism for Nucleic Acid Aging and Age-related Dysfunction in Gene Expression. Proc. Natl. Acad. Sci. U.S.A. 81, 105-109.
7. Chaudhuri, N. C., and Kool, E. T. (1995) An Efficient Method for the Synthesis of Aromatic C-Nucleosides. Tetrahedron Lett. 36, 1795-1798 and corrigendum Tetrahedron Lett. 36, 4910.
8. Chaw, Y. F. M., Crane, L. E., Lange, P., and Shapiro, R. (1980) Isolation and Identification of Cross-Links from Formaldehyde-Treated Nucleic Acids. Biochemistry 19, 5525-5531.
9. Chernomordik, L. V., Frolov, V. A., Leikina, E., Bronk, P., and Zimmerberg, J. (1998) The Pathway of Membrane Fusion Catalyzed by Influenza Hemagglutinin: Restriction of Lipids, Hemifusion, and Lipidic Fusion Pore Formation. J. Cell. Biol. 140, 1369-1382.
10. Coombs, M. M., and Livingston, D. C. (1969) Reaction of Apurinic Acid with Aldehyde Reagents. Biochim. Biophys. Acta 174, 161-173.
11. Dechamps, M., and Sonveaux, E. (1998) Aldehydo-Oligonucleotides for Bioconjugation. Nucleosides, Nucleotides 17, 697-709.
12. Fox, J. J., Yung, N. C., Wempen, I., and Hoffer, M. (1961) Nucleosides XII. Direct Synthesis of 2′-Deoxycytidine and its α-Anomer. J. Am. Chem. Soc. 83, 4066-4070.
13. François, P., Sonveaux, E., and Touillaux, R. (1990) A High Field NMR Study of 2′-Deoxyribo-C-nucleosides. Nucleosides Nucleotides 9, 379-382.
14. François P., Muzzin, P., Dechamps, M., and Sonveaux, E. (1994) The Incorporation of Flexible Hydrophobic Chains into Double-stranded DNA: the Consequences for Stability. New J. Chem. 18, 649-657.
15. Gao, K., and Orgel, L. E. (1999) Nucleic Acid Duplexes Incorporating a Dissociable Covalent Base Pair. Proc. Natl. Acad. Sci. 96, 14837-14842.
16. 5. Acta Crystallogr. C41, 720-722.
17. Huang, H., and Hopkins, P. B. (1993) DNA Interstrand Cross-Linking by Formaldehyde: Nucleotide Sequence Preference and Covalent Structure of the Predominant Cross-Link Formed in Synthetic Oligonucleotides. J. Am. Chem. Soc. 115, 9402-9408.
18. Hurd, C. D., and Holysz, R. P. (1950) Reactions of Polyacylglycosyl Halides with Organocadmium Reagents. J. Am. Chem. Soc. 72, 2005-2008.
19. Jacobsen, E. N., Marko, I., Mungall, W. S., Schröder, G., Sharpless, K. B. (1988) Asymmetric Dihydroxylation via Ligand-Accelerated Catalysis. J. Am. Chem. Soc. 110, 1968-1970.
20. Klein, R. S., Kotick, M. P., Watanabe, K. A., and Fox, J. J. (1971) Nucleosides LXXIII. Ribosyl Analogues of Chloramphenicol. J. Org. Chem. 36, 4113-4116.
21. Kremsky, J. N., Wooters, J. L., Dougherty, J. P., Meyers, R. E., Collins, M., and Brown, E. L. (1987) Immobilization of DNA via Oligonucleotides Containing an Aldehyde or Carboxylic Acid Group at the 5′ Terminus. Nucleic Acids Res. 15, 2891-2909.
22. Lemaitre, M., Bayard, B., and Lebleu, B. (1987) Specific Antiviral Activity of a Poly(-L-lysine)-conjugated Oligodeoxyribonucleotide Sequence Complementary to Vesicular Stomatitis Virus N Protein in mRNA Initiation Site. Proc. Natl. Acad. Sci. U.S.A. 84, 648-652.
23. Lane, C. F. (1975) Sodium Cyanoborohydride - A Highly Selective Reducing Agent for Organic Functional Group. Synthesis 135-146.
24. Liuzzi, M., and Talpaert-Borlé, M. (1985) A New Approach to the Study of Base-excision Repair Pathway Using Methoxyamine. J. Biol. Chem. 260, 5252-5258.
25. Liuzzi, M., Weinfeld, M., and Paterson, M. C. (1987) Selective Inhibition by Methoxyamine of the Apurinic/ Apyrimidinic Endonuclease Activity Associated with Pyrimidine Dimer-DNA Glycosylases from Micrococcus luteus and Bacteriophage T4. Biochemistry 26, 3315-3321.
26. Maruyama, A., Watanabe, H., Ferdous, A., Katoh, M., Ishihara, T., and Akaike, T. (1998) Characterization of Interpolyelectrolyte Complexes between Double-Stranded DNA and Polylysine Comb-Type Copolymers Having Hydrophilic Side Chains. Bioconjugate Chem. 9, 292-299.
27. Matsuda, T., Kawanishi, M., Yagi, T., Matsui, S., and Takebe, H. (1998) Specific Tandem GG to TT Base Substitutions Induced by Acetaldehyde Are Due to Intra-Strand Cross-links between Adjacent Guanine Bases. Nucleic Acids Res., 26, 1769-1774.
28. Millican, T. A., Mock, G. A., Chauncey, M. A., Patel, T. P., Eaton, M. A. W., Gunning, J., Cutbush, S. D., Neidle, S., and Mann, J. (1984) Synthesis and Biophysical Studies of Short Oligodeoxynucleotides with Novel Modifications: a Possible Approach to the Problem of Mixed Base Oligodeoxynucleotide Synthesis. Nucleic Acids Res. 12, 7435-7453.
29. Nadeau, J. G., Singleton, C. K., Kelly, G. B., Weith, H. L., and Gough, G. R. (1984) Use of Ribonucleosides as Protecting Groups in Synthesis of Polynucleotides with Phosphorylated Terminals. Biochemistry 23, 6153-6259.
30. Ness, R. K., MacDonald, D. L., Fletcher Jr., H. G. (1961) 2-Deoxy-D-ribose VII. Crystalline 2-Deoxy-3,5-di-O-p-nitrobenzoyl-D-ribosyl Chloride and Related Derivatives. J. Org. Chem. 26, 2895-2899.
31. Peyrottes, S., Mestre, B., Burlina, F., and Gait, M. J. (1998) The Synthesis of Peptide-Oligonucleotide Conjugates by a Fragment Coupling Approach. Tetrahedron 54, 12513-12522.
32. Ren, R. X.-F., Chaudhuri, N. C., Paris, P. L., Rumney IV, S., and Kool, E. T. (1996) Naphthalene, Phenanthrene, and Pyrene as DNA Base Analogues: Synthesis, Structure, and Fluorescence in DNA. J. Am. Chem. Soc. 118, 7671-7678.
33. Robins, M. J., Wilson, J. S., and Hansske, F. (1983) Nucleic Acid Related Compounds 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Stereoselective Conversion of Ribonucleosides to 2′-Deoxynucleosides. J. Am. Chem. Soc. 105, 4059-4065.
34. Shinozuka, K., Kohgo, S., Ozaki, H., and Sawai, H. (2000) Multi-Functionalization of Oligodeoxynucleotide: a Facile Postsynthetic Modification Technique for the Preparation of Oligodeoxynucleotides with Two Different Functional Molecules. J. Chem. Soc., Chem. Commun. 59-60.
35. a-Fmoc-cysteine(S-thiobutyl) Derivatized Oligodeoxynucleotides for the Preparation of Oligodeoxynucleotide-Peptide Hybrid Molecules. Bioconjugate Chem. 9, 466-475.
36. Strässler, C., Davis, N. E., and Kool, E. T. (1999) Novel Nucleoside Analogues with Fluorophores Replacing the DNA Base. Helv. Chim. Acta 82, 2160-2171.
37. 14C)Methoxyamine. A Method for the Quantitative Assay of AP Sites in DNA. Biochim. Biophys. Acta 740, 410-416.
38. Teigelkamp, S., Ebel, S., Will, D. W., Brown, T., and Beggs, J. D. (1993) Branched Poly-labelled Oligonucleotides: Enhanced Specificity of Fork-shaped Biotinylated Oligoribonucleotides for Antisense Affinity Selection. Nucleic Acids Res. 21, 4651-4652.
39. Trévisiol, E., Renard, A., Defrancq, E., and Lhomme, J. (1997) The Oxyamino-Aldehyde Coupling Reaction: An Efficient Method for the Derivatization of Oligonucleotides. Tetrahedron Lett. 38, 8687-8690.
40. Urata, H., and Akagi, M. (1993) A Convenient Synthesis of Oligonucleotides with a 3′-Phosphoglycolate and 3′-Phosphoglycaldehyde Terminus. Tetrahedron Lett. 34, 4015-4018.
41. Vasseur, J.-J., Rayner, B., and Imbach, J.-L. (1986) Preparation of a Short Synthetic Apurinic Oligonucleotide. Biochem. Biophys. Res. Commun. 134, 1204-1208.
42. Westfall, D. A., Flores, R. R., Negrete, G. R., Martinez, A. O., and Haro, L. S. (1998) High-Resolution Polyacrylamide Gel Electrophoresis of Carbohydrates Derivatized with a Visible Dye. Anal. Biochem. 265, 232-237.
43. Wu, T., and Ogilvie, K. K. (1990) A Study on the Alkylsilyl Groups in Oligoribonucleotide Synthesis. J. Org. Chem. 55, 4717-4724.
44. Zhao, Q., Tolmachev, V., Carlsson, J., Lundqvist, H., Sundin, J., Janson, J.-C., and Sundin, A. (1999) Effects of Dextranation on the Pharmacokinetics of Short Peptides. A PET Study on mEGF. Bioconjugate Chem. 10, 938-946.