2-Hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8561-8564

  Bell, Andrew A ^a   Pickering, Lea ^a   Watson, Alison A ^b   Nash, Robert J ^b   Griffiths, Rhodri C ^c   Jones, M George ^c   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ABERYSTWYTH UNIVERSITY   (United Kingdom)

^c ABERYSTWYTH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CASTANOSPERMINE DERIVATIVE; GLYCOSIDASE; SWAINSONINE;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030592829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01956-9     Document Type: Article

References (18)

1. 1. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Picasso, S., Chen, Y., Vogel, P., Carbohydr. Lett., 1994, 1, 1; Furneaux, R. H., Gainsford, G. J., Mason, J. M., Tyler, P. C., Tetrahedron, 1995, 51, 12611; Goti, A., Cardona, F., Brandi, A., Picasso, S., Vogel, P., Tetrahedron: Asymm., 1996, 7, 1659; Asano, N., Kizu, H., Oseki, Tomioka, E., Matsui, K., Okamoto, M., Baba, M., J. Med. Chem., 1995, 38, 2349.
2. 1. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Picasso, S., Chen, Y., Vogel, P., Carbohydr. Lett., 1994, 1, 1; Furneaux, R. H., Gainsford, G. J., Mason, J. M., Tyler, P. C., Tetrahedron, 1995, 51, 12611; Goti, A., Cardona, F., Brandi, A., Picasso, S., Vogel, P., Tetrahedron: Asymm., 1996, 7, 1659; Asano, N., Kizu, H., Oseki, Tomioka, E., Matsui, K., Okamoto, M., Baba, M., J. Med. Chem., 1995, 38, 2349.
3. 1. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Picasso, S., Chen, Y., Vogel, P., Carbohydr. Lett., 1994, 1, 1; Furneaux, R. H., Gainsford, G. J., Mason, J. M., Tyler, P. C., Tetrahedron, 1995, 51, 12611; Goti, A., Cardona, F., Brandi, A., Picasso, S., Vogel, P., Tetrahedron: Asymm., 1996, 7, 1659; Asano, N., Kizu, H., Oseki, Tomioka, E., Matsui, K., Okamoto, M., Baba, M., J. Med. Chem., 1995, 38, 2349.
4. 1. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Picasso, S., Chen, Y., Vogel, P., Carbohydr. Lett., 1994, 1, 1; Furneaux, R. H., Gainsford, G. J., Mason, J. M., Tyler, P. C., Tetrahedron, 1995, 51, 12611; Goti, A., Cardona, F., Brandi, A., Picasso, S., Vogel, P., Tetrahedron: Asymm., 1996, 7, 1659; Asano, N., Kizu, H., Oseki, Tomioka, E., Matsui, K., Okamoto, M., Baba, M., J. Med. Chem., 1995, 38, 2349.
5. 1. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Picasso, S., Chen, Y., Vogel, P., Carbohydr. Lett., 1994, 1, 1; Furneaux, R. H., Gainsford, G. J., Mason, J. M., Tyler, P. C., Tetrahedron, 1995, 51, 12611; Goti, A., Cardona, F., Brandi, A., Picasso, S., Vogel, P., Tetrahedron: Asymm., 1996, 7, 1659; Asano, N., Kizu, H., Oseki, Tomioka, E., Matsui, K., Okamoto, M., Baba, M., J. Med. Chem., 1995, 38, 2349.
6. 2. Molyneux, R. J., Roitman, J., Dunnheim, G., Szumilo, T., Elbein, A.D., Arch. Biochem. Biophys., 1986, 251, 450.
7. 3. Nash, R. J., Thomas, P. I., Waigh, R. D., Fleet, G. W. J., Wormald, M. R., Lilley, P. M. D., Watkin, D. J., Tetrahedron Lett., 1994, 35, 7849.
8. 4. Wormald, M. R., Nash, R. J., Watson, A. A., Bhadoria, B. K., Langford, R., Sims, M., Fleet, G. W. J., Carbohydr. Lett., 1996, 2, in press.
9. 5. Bell, A. A., Nash, R. J., Fleet, G. W. J., Tetrahedron: Asymm., 1996, 7, 595.
10. 6. Berger, A., Dax, K., Gradnig, G., Grassberger, V, Stutz, A. E., Ungerank, M., Legler, G., Bause, E., Bioorg. Med. Chem. Lett., 1992, 2, 27; Baudat, A., Picasso, A., Vogel, P., Carbohydr. Res., 1996, 281, 277.
11. 6. Berger, A., Dax, K., Gradnig, G., Grassberger, V, Stutz, A. E., Ungerank, M., Legler, G., Bause, E., Bioorg. Med. Chem. Lett., 1992, 2, 27; Baudat, A., Picasso, A., Vogel, P., Carbohydr. Res., 1996, 281, 277.
12. 7. Unless otherwise stated, all specific rotations were measured in chloroform.
13. +, 100%).
14. +, 100%)
15. +100%.
16. m 1.1 mM), for further details of the assays, see following paper.
17. 12. Oishi, T., Iwakuma, T., Hirama, M., Ito, S., Synlett, 1995, 404; no enzyme inhibition studies for L-swainsonine were reported in this paper.
18. 13. This work has been supported by graduate studentships from the Medical Research Council AIDS Committee and BBSRC, and by an EPSRC Post-doctoral Fellowship.