Synthesis of diastereomeric mixtures of 5′-C-hydroxymethylthymidine and introduction of a novel class of C-hydroxymethyl functionalised oligodeoxynucleotides

Acta Chemica Scandinavica

Volumn 50, Issue 12, 1996, Pages 1157-1163

  Fensholdt, Jef ^a   Wengel, Jesper ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

5' C HYDROXYMETHYLTHYMIDINE; 5'-C-HYDROXYMETHYLTHYMIDINE; DRUG DERIVATIVE; OLIGODEOXYRIBONUCLEOTIDE; OSMIUM TETRAOXIDE; THYMIDINE;

ARTICLE; CHEMICAL STRUCTURE; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; STEREOISOMERISM; SYNTHESIS;

BASE SEQUENCE; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; OSMIUM TETROXIDE; STEREOISOMERISM; THYMIDINE;

EID: 0030340080     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.50-1157     Document Type: Article

References (26)

1. Uhlmann, E. and Peyman, A. Chem. Rev. 90 (1990) 543.
2. Englisch, U. and Gauss, D. H. Angew. Chem. Int. Ed. Engl. 30 (1991) 613.
3. Beaucage, S. L. and Iyer, R. P. Tetrahedron 49 (1993) 6123.
4. Wagner, R. W. Nature 372 (1994) 333.
5. De Mesmaeker, A., Häner, R., Martin, P. and Moser, H. E. Acc. Chem. Res. 28 (1995) 366.
6. Jørgensen, P. N., Stein, P. C. and Wengel, J. J. Am. Chem. Soc. 116 (1994) 2231.
7. Jørgensen, P. N., Svendsen, M. L., Scheuer-Larsen, C. and Wengel, J. Tetrahedron 51 (1995) 2155.
8. Fensholdt, J., Thrane, H. and Wengel, J. Tetrahedron Lett. 36 (1995) 2535.
9. Thrane, H., Fensholdt, J., Regner, M. and Wengel, J. Tetrahedron 51 (1995) 10389.
10. Bhat, C. C., Bhat, K. V. and Zorbach, W. W. Carbohydr. Res. 8 (1968) 368.
11. Synthesis of alkene 1 has been described in a patent but no characterisation data were reported: Weis, A. L., Hausheer, F. H., Frederick, H., Chaturvedula, P. V. C., Delecki, D. J., Cavanaugh, P. F., Jr., Moskwa, P. S. and Oakes, F. T. PCT Int. Appl. WO 92 02,534; Chem. Abstr. 117:105700r.
12. Jones, G. H., Taniguchi, M., Tegg, D., Moffatt, J. G. J. Org. Chem. 44 (1919) 1309.
13. Ray, R. and Matteson, D. S. Tetrahedron Lett. 21 (1980) 449.
14. Barvian, M. R. and Greenberg, M. M. J. Org. Chem. 58 (1993) 6151.
15. Wengel, J., Svendsen, M. L., Jørgensen, P. N. and Nielsen, C. Nucleosides Nucleotides 14 (1995) 1465.
16. Jacobsen, E. N., Markó, I., Mungall, W. S., Schröder, G., and Sharpless, K. B. J. Am. Chem. Soc. 110 (1988) 1968.
17. Sharpless, K. B., Amberg, W., Beller, M., Chen, H., Hartung, J., Kawanami, Y., Lübben, D., Manoury, E., Ogino, Y., Shibata, T. and Ukita, T. J. Org. Chem. 56 (1991) 4585.
18. Sharpless, K. B., Amberg, W., Bennani, Y. L., Crispino, G. A., Hartung, J., Jeong, K.-S., Kwong, H.-L., Morikawa, K., Wang, Z.-M., Xu, D. and Zhang, X.-L. J. Org. Chem. 57 (1992) 2768.
19. Saha, A. K., Caulfield, T. J., Hobbs, C., Upson, D. A., Waychunas, C. and Yawman, A. M. J. Org. Chem. 60 (1995) 785.
20. Silylation of the 6′-O-hydroxy group eliminates the risk of strand cleavage during ammonia treatment: Hardy, P. M., Holland, D., Scott, S., Garman, A. J., Newton, C. R. and McLean, M. J. Nucleic Acids Res. 22 (1994) 2998.
21. McBride, L. J. and Caruthers, M. H. Tetrahedron Lett. 24 (1983) 245.
22. Sinha, N. D., Biernat, J. and Köster, H. Tetrahedron Lett. 24 (1983) 5843.
23. Caruthers, M. H. Science 230 (1985) 281.
24. Nielsen, P., Kirpekar, F. and Wengel, J. Nucleic Acids Res. 22 (1994) 703.
25. Newman, P. C., Nwosu, V. U., Williams, D. M., Cosstick, R., Seela, F. and Connolly, B. A. Biochemistry 29 (1990) 891.
26. Svendsen, M. L., Wengel, J., Dahl, O., Kirpekar, F. and Roepstorff, P. Tetrahedron 49 (1993) 11341.