Synthesis of oligonucleotides containing 3'-alkylcarboxylic acids using a palladium labile oligonucleotide solid phase synthesis support

Bioconjugate Chemistry

Volumn 8, Issue 2, 1997, Pages 99-102

  Matray, Tracy J ^a   Yoo, Dong Jin ^a   McMinn, Dustin L ^a   Greenberg, Marc M ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOPOLYMERS; MASS SPECTROMETRY; PALLADIUM; SYNTHESIS (CHEMICAL);

ANION EXCHANGE; CLEAVAGE REACTION; CONDITION; ELECTROSPRAY MASS SPECTROMETRY; ENZYMATIC DIGESTIONS; EXPERIMENTAL ERRORS; ISOLATED YIELD; NO REDUCTION; PHOSPHORAMIDITES; SOLID PHASE SYNTHESIS;

OLIGONUCLEOTIDES;

EID: 0342710412     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970013a     Document Type: Article

References (22)

1. Beaucage, S. L., and Iyer, R. P. (1993) The Synthesis of Modified Oligonucleotides by the Phosphoramidite Approach and Their Applications. Tetrahedron 49, 6123-6194.
2. Truffert, J-C., Lorthioir, O., Asseline, U., Thuong, N. T., and Brack, A. (1994) On-Line Solid Phase Synthesis of Oligonucleotide-Peptide Hybrids Using Silica Supports. Tetrahedron Lett. 35, 2353-2356.
3. de la Torre, B. G., Aviñó, A., Tarrason, G., Piulats, J., Albericio, F., and Eritja, R. (1994) Stepwise Solid-Phase Synthesis of Oligonucleotide-Peptide Hybrids. Tetrahedron Lett. 35, 2733-2736.
4. MacKellar, C., Graham, D., Will, D. W., Burgess, S., and Brown, T. (1992) Synthesis and Physical Properties of Anti-HIV Antisense Oligonucleotides Bearing Terminal Lipophilic Groups. Nucleic Acids Res. 20, 3411-3417.
5. Haralambidis, J., Angus, K., Pownall, S., Duncan, L., Chai, M., and Tregear, G. W. (1990) The Preparation of Polyamide Oligonucleotide Probes Containing Multiple Non-Radioactive Labels. Nucleic Acids Res. 18, 501-505.
6. Jones, D. S., Hachmann, J. P., Osgood, S. A., Hayag, M. S., Barstad, P. A., Iverson, G. M., and Coutts, S. M. (1994) Conjugates of Double-Stranded Oligonucleotides With Poly(ethylene glycol) and Keyhole Limpet Hemocyanin: A Model for Treating Systemic Lupus Erythematosus. Bioconjugate Chem. 5, 390-399.
7. Leonetti, J-P., Degols, G., and Lebleu, B. (1990) Biological Activity of Oligonucleotide-Poly(L-lysine) Conjugates: Mechanism of Cell Uptake. Bioconjugate Chem. 1, 149-153.
8. Letsinger, R. L., Zhang, G., Sun, D. K., Ikeuchi, T., and Sarin, P. S. (1989) Cholesteryl-Conjugated Oligonucleotides: Synthesis, Properties, and Activity as Inhibitors of Replication of Human Immunodeficiency Virus in Cell Culture. Proc. Natl. Acad. Sci. U.S.A. 86, 6553-6556.
9. Goodchild, J. (1990) Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-187.
10. Ghosh, S. S., and Musso, G. F. (1987) Covalent Attachment of Oligonucleotides to Solid Supports. Nucleic Acids Res. 15, 5353-5372.
11. Bischoff, R., Coull, J. M., and Regnier, F. E. (1987) Introduction of 5′-Terminal Functional Groups Into Synthetic Oligonucleotides For Selective Immobilization. Anal. Biochem. 164, 336-344.
12. McMinn, D. L., and Greenberg, M. M. (1996) Novel Solid Phase Synthesis Supports For The Preparation of Oligonucleotides Containing 3′-Alkyl Amines. Tetrahedron 52, 3827-3840.
13. Venkatesan, H., and Greenberg, M. M. (1996) Improved Utility of Photolabile Solid Phase Synthesis Supports For The Synthesis of Oligonucleotides Containing 3′-Hydroxyl Termini. J. Org. Chem. 61, 525-529.
14. Yoo, D. J., and Greenberg, M. M. (1995) Synthesis of Oligonucleotides Containing 3′-Alkyl Carboxylic Acids Using Universal Photolabile Solid Phase Synthesis Supports. J. Org. Chem. 60, 3358-3364.
15. Matray, T. J., Yoo, D. J., and Greenberg, M. M. (1996) Palladium Labile Oligonucleotide Synthesis Supports. Abstracts of Papers, 211th National Meeting of the American Chemical Society, New Orleans, LA, Division of Organic Chemistry Abstract 119, American Chemical Society, Washington, DC.
16. Zhang, X., and Jones, R. A. (1996) Solid-Phase Synthesis of Peptide Aminoalkylamides Using An Allyl Linker. Tetrahedron Lett. 37, 3789-3790.
17. Hayakawa, Y., Wakabayashi, S., Kato, H., and Noyori, R. (1990) The Allylic Protection Method in Solid-Phase Oligonucleotide Synthesis. An Efficient Preparation of Solid-Anchored DNA Oligomers. J. Am. Chem. Soc. 112, 1691-1696.
18. Seitz, O., and Kunz, H. (1995) A Novel Allylic Anchor for Solid-Phase Synthesis-Synthesis of Protected and Unprotected O-Glycosylated Mucin-Type Glycopeptides. Angew. Chem., Int. Ed. Engl. 34, 803-805.
19. Kunz, H., and Dombo, B. (1988) Solid Phase Synthesis of Peptides and Glycopeptides on Polymeric Supports With Allylic Anchor Groups. Angew. Chem., Int. Ed. Engl. 27, 711-713.
20. L-Williams, P., Merzouk, A., Guibé, F., Albericio, F., and Giralt, E. (1994) Solid-Phase Synthesis of Peptides Using Allylic Anchoring Groups 2. Palladium-Catalysed Cleavage of Fmoc-Protected Peptides. Tetrahedron Lett. 35, 4437-4440.
21. Kaljuste, K, and Undén, A. (1996) Solid-Phase Synthesis of Peptide Aminoalkylamides Using an Allyl Linker. Tetrahedron Lett. 37, 3031-3034.
22. Nicolaou, K. C., Prasad, C. V. C., Somers, P. K., and Hwang, C-K. (1989) Activation of 6-Endo Over 5-Exo Hydroxyl Epoxide Opening. Stereoselective and Ring Selective Synthesis of Tetrahydrofuran and Tetrahydropyran Systems. J. Am. Chem. Soc. 111, 5330-5334.