An Approach to the Solid Phase Synthesis of Oligonucleotides Containing N-Acylphosphoramidate Internucleosidic Linkages

Synlett

Volumn 1996, Issue 8, 1996, Pages 769-771

  Filippov, Dmitri ^a   Meeuwenoord, Nico J ^a   Van Der Marel, Gijs A ^a   Efimov, Vladimir A ^b   Kuyl Yeheskiely, Esther ^a   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002318771     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5511     Document Type: Article

References (24)

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2. Gryaznov, S.; Letsinger, R. L. Nucleic Acids Res. 1992, 20, 3403-3409. Bannwarth, W. Helv. Chim. Acta, 1988, 71, 1517-1527. Mungall, W. S.; Green, G. L.; Heavner, G. A.; Letsinger, R. L. J. Org. Chem. 1975, 40, 1659-1662.
3. Gryaznov, S.; Letsinger, R. L. Nucleic Acids Res. 1992, 20, 3403-3409. Bannwarth, W. Helv. Chim. Acta, 1988, 71, 1517-1527. Mungall, W. S.; Green, G. L.; Heavner, G. A.; Letsinger, R. L. J. Org. Chem. 1975, 40, 1659-1662.
4. Böhringer, M. P.; Graff, D.; Caruthers, H. M. Tetrahedron Lett. 1993, 34, 2723-2726. Morr, M.; Ernst, L.; Schomburg, D. Liebigs Ann. Chem. 1991, 615-631.
5. Böhringer, M. P.; Graff, D.; Caruthers, H. M. Tetrahedron Lett. 1993, 34, 2723-2726. Morr, M.; Ernst, L.; Schomburg, D. Liebigs Ann. Chem. 1991, 615-631.
6. Cosstick, R.; Vyle, J. S. Nucleic Acids Res. 1990, 18, 829-835. Chladek, S.; Nagyvary, J. J. Am. Chem. Soc. 1972, 94, 2079-2085. Kresse, J.; Nagpal, K. L.; Nagyvary, J.; Uchic, J. T. Nucleic Acids Res. 1975, 2, 1-9.
7. Cosstick, R.; Vyle, J. S. Nucleic Acids Res. 1990, 18, 829-835. Chladek, S.; Nagyvary, J. J. Am. Chem. Soc. 1972, 94, 2079-2085. Kresse, J.; Nagpal, K. L.; Nagyvary, J.; Uchic, J. T. Nucleic Acids Res. 1975, 2, 1-9.
8. Cosstick, R.; Vyle, J. S. Nucleic Acids Res. 1990, 18, 829-835. Chladek, S.; Nagyvary, J. J. Am. Chem. Soc. 1972, 94, 2079-2085. Kresse, J.; Nagpal, K. L.; Nagyvary, J.; Uchic, J. T. Nucleic Acids Res. 1975, 2, 1-9.
9. Tate, M. E.; Murphy, P. J.; Roberts, W. P.; Kerr, A. Nature 1979, 280, 697-699.
10. Guijarro, J. I.; González-Pastor, J. E.; Baleux, F.; Millán, J. L. S.; Castilla, M. A.; Rico, M.; Moreno, F.; Delepierre, M. J. Biol. Chem. 1995, 270, 23520-23532.
11. Uramoto, M.; Kim, C. J.; Shin-ya, K.; Kusakabe, H; Isono, K.; Phillips, D. R.; McCloskey, J. A. J. Antibiot. 1991, 44, 375-381.
12. Robles, J.; Pedroso, E.; Grandas, A. J. Org. Chem. 1995, 60, 4856-4861. Grandas, A.; Robles, J.; Pedroso, E. Nucleosides & Nucleotides, 1995, 14, 825-828.
13. Robles, J.; Pedroso, E.; Grandas, A. J. Org. Chem. 1995, 60, 4856-4861. Grandas, A.; Robles, J.; Pedroso, E. Nucleosides & Nucleotides, 1995, 14, 825-828.
14. Abbreviations used : BOP, benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; CNE, 2-cyanoethyl; DMAP, 4-dimethylaminopyridine; DIEA, N,N-diisopropylethylamine; DMT, 4,4′-dimethoxytrityl; TBS, tert-butyldimethylsilyl; TCA, trichloroacetic acid; TEA, triethylamine; TEAA, triethylammonium acetate.
15. Castro, B.; Dormoy, J.R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219-1222.
16. 3CN) 119.01, 118.77.
17. Efimov, V. A.; Kalinkina A. L.; Chakhmakhcheva, O. G. Bioorg. Khim. 1996, 22, 149-152. 5-MMT is commercially available from Aldrich.
18. 3OD) δ -1.80, -1.98, -2.09, -2.34, -2.55, -2.98.
19. 2/MeOH/25% aq. ammonia (14/5/1 v/v/v).
20. +; (negative mode) 636 (M-H).
21. +-salt) which was identical in all respects to the corresponding monomeric chain fission product.
22. ®).
23. R 12.6 min.
24. Kuijpers, W. H. A.; Huskens, J.; van Boekel, C. A. A. Tetrahedron Lett. 1990, 31, 6729-6732.