Recent progress in oligonucleotide synthesis

Acta Biochimica Polonica

Volumn 43, Issue 1, 1996, Pages 37-44

  Pfleiderer, Wolfgang ^a   Matysiak, Stefan ^a   Bergmann, Frank ^a   Schnell, Ralf ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

2 (2 nitrophenyl)ethoxycarbonyl group; 2 (4 nitrophenyl)ethyl group; 3 fluoro 4 2 (4 nitrophenyl)ethoxycarbonyloxybenzyl group; Acetal protecting groups; Dansylethoxycarbonyl group; Oligonucleotide synthesis; Phosphoramidite approach; Solid phase synthesis

Indexed keywords

ACETAL DERIVATIVE; DANSYL CHLORIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OLIGODEOXYRIBONUCLEOTIDE; OLIGONUCLEOTIDE; OLIGORIBONUCLEOTIDE;

CHEMICAL STRUCTURE; REVIEW; SYNTHESIS;

ACETALS; DANSYL COMPOUNDS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; OLIGONUCLEOTIDES; OLIGORIBONUCLEOTIDES;

EID: 0029688728     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.1996_4515     Document Type: Article

References (27)

1. Dorman, M.A., Noble, S.A., McBride, L.J. & Caruthers, M.H. (1984) Synthesis of oligodeoxynucleotides and oligodeoxynucleotide analogs using phosphoramidite intermediates. Tetrahedron 40, 95-102.
2. Köster, H., Biernat, J., McManus, J., Wolter, A., Stumpe, A., Narang, Ch.K. & Sinha, N.D. (1984) Synthesis of oligodeoxynucleotides on controlled pore glass (CPG) using phosphate and a new phosphite triester approach. Tetrahedron 40, 103-112.
3. Brown, T. & Brown, D.J.S. (1991) Modern machine-aided methods of oligodeoxyribonucleotide synthesis; in Oligonucleotides and Analogues (Eckstein, F., ed.) pp. 1-24, IRL Press, Oxford.
4. Gait, M.J., Pritchard, C. & Slim, G. (1991) Oligoribonucleotide synthesis; in Oligonucleotides and Analogues (Eckstein, F., ed.) pp. 25-48, IRL Press, Oxford.
5. Usman, N., Ogilvie, K.K., Jiang, M.-Y. & Cedergren, R.J. (1987) Automated chemical synthesis of long oligoribonucleotides using 2′-O-si-lylated ribonucleoside 3′-O-phosphoramidites on a controlled-pore glass support: Synthesis of a 43-nucleotide sequence similar to the 3′-half molecule of an Escherichia coli formylmethionine tRNA. J. Am. Chem. Soc. 109, 7845-7854.
6. Ogilvie, K.K., Usman, N., Nicoghosian, K. & Cedergren, R.L. (1988) Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity. Proc. Natl. Acad. Sci. U.S.A. 85, 5764-5768.
7. Scaringe, S.A., Francklyn, C. & Usman, N. (1990) Chemical synthesis of biologically active oligoribonucleotides using β-cyanoethyl protected ribonucleoside phosphoramidites. Nucleic Acids Res. 18, 5433-5441.
8. Wu, T. & Ogilvie, K.K. (1990) A study on the alkylsilyl groups in oligoribonucleotides synthesis. J. Org. Chem. 55, 4717-4724.
9. Little, M.H., Wright, P.B., Sinha, N.D., Bain, J.D. & Chamberlin, A.R. (1991) New nucleoside phosphoramidites and coupling protocols for solid-phase RNA synthesis. J. Org. Chem. 56, 4608-4615.
10. Beaucage, S.L. & Iyer, R.P. (1992) Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron 48, 2223-2311.
11. Gasparutto, D., Livache, T., Bazin, M., Duplaa, A.M., Guy, A., Khorlin, A., Molko, D., Roget, A. & Teoule, R. (1992) Chemical synthesis of a biologically active natural tRNA with its minor bases. Nucleic Acids Res. 20, 5159-5166.
12. Gasparutto, D., Molko, D. & Teoule, R. (1990) Studies on the formation of the internucleotidic bond in RNA synthesis using dialkylamino phosphoroamidites. Nucleosides & Nucleotides 9, 1087-1098.
13. Little, H.M. (1993) Chain cleavage during deprotection of RNA synthesized by the 2′-O′-trialkylsilyl protection strategy. Nucleosides & Nucleotides 12, 95-106.
14. Rao, M.V., Reese, C.B., Schehlmann, V. & Yu, P.S. (1993) Use of the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) protecting group in the solid-phnse synthesis of oligo- and poly-ribonucleotides. J. Chem. Soc. Perkin Trans. 1, 43-55.
15. Capaldi, D.C. & Reese, C.B. (1994) Use of the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting groups in oligoribonucleotide synthesis: Stability of internucleotide linkages to aqueous acid. Nucleic Acids Res. 22, 2209-2216.
16. Stengele, K.P. & Pfleiderer, W. (1990) Improved synthesis of oligodeoxyribonucleotides. Tetrahedron Lett. 31, 2549-2552.
17. Himmelsbach, F., Schulz, B.S., Trichtinger, T., Charubala, R. & Pfleiderer, W. (1984) The p-nitrophenylethyl (NPE) group. A versatile new blocking group for phosphate and aglycone protection in nucleosides and nucleotides. Tetrahedron 40, 59-72.
18. Reese, C.B., Saffhill, R. & Sulston, J.E. (1967) A symmetrical alternative to the tetrahydropyranyl protecting group. J. Am. Chem. Soc. 89, 3366-3368.
19. Bergmann, F. & Pfleiderer, W. (1994) The 2-dansylethoxycarbonyl (Dnseoc) group for protection of the 5′-hydroxyl function in oligodeoxyribonucleotide synthesis. Helv. Chim. Acta 76, 203-215.
20. Bergmann, F. & Pfleiderer, W. (1994) The 2-dansylethoxycarbonyl (Dnseoc) group for protection of the 5′-hydroxy function in oligoribonucleotide synthesis. Helv. Chim. Acta 77, 481-501.
21. Bergmann, F. & Pfleiderer, W. (1944) Solid-phase synthesis of oligoribonucleotides using the 2-dansylethoxycarbonyl (Dnseoc) group for 5′-hydroxy protection. Helv. Chim. Acta 77, 988-998.
22. Chattopadhyaya, J.B. & Reese, C.B. (1978) The 9-phenylxanthen-9-yl protecting group. J. Chem. Soc., Chem. Commun. 639-640.
23. Reese, C.B. & Skone, P.A. (1985) Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions. Nucleic Acids Res. 13, 5215-5231.
24. Reese, C.B., Serafinowska, H.T. & Zappia, G. (1986) An acetal group suitable for the protection of 2′-hydroxy functions in rapid oligoribonucleotide synthesis. Tetrahedron Lett. 27, 2291-2294.
25. Rao, T.S., Reese, C.B., Serafinoska, H.T., Takaku, H. & Zappia, G. (1987) Solid phase synthesis of the 3′-terminal nonadecaribonucleoside octadecaphosphate sequence of yeast alanine transfer ribonucleic acid. Tetrahedron Lett. 28, 4897-4900.
26. Sakatsume, O., Yamaguchi, T., Ishikawa, M., Hirao, I., Miura, K. & Takaku, H. (1991) Solid-phase synthesis of oligoribonucleotides by the phosphoramidite approach using 2′-O-1-(2-chloroethoxy)ethyl protection. Tetrahedron 47, 8717-8728.
27. Sakatsume, O., Ogawa, T., Hosaka, H., Kawashima, M., Takaki, M. & Takaku, H. (1991) Synthesis and properties of non-hammerhead RNA 1-(2-chloroethoxy)ethyl group for the protection of 2′-hydroxyl function. Nucleosides & Nucleotides 10, 141-153.