Generalized anomeric effect in action: Synthesis and evaluation of stable reducing indolizidine glycomimetics as glycosidase inhibitors

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 136-143

  Díaz Pérez, Víctor M ^a   García Moreno, M Isabel ^a   Mellet, Carmen Ortiz ^a   Fuentes, José ^a   Díaz Arribas, Juan C ^b   Cañada, F Javier ^b   García Fernández, José M ^c  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5,6,7,8 TETRAACETOXY 2 OXA 3 OXOINDOLIZIDINE; 5,6,7,8 TETRAHYDROXY 2 OXA 3 THIOXOINDOLIZIDINE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR STABILITY;

CARBOHYDRATE CONFORMATION; ENZYME INHIBITORS; EVALUATION STUDIES; GLYCOSIDE HYDROLASES; INDOLIZINES; MOLECULAR MIMICRY; REDUCING AGENTS; SPECTRUM ANALYSIS;

EID: 0242452497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991242o     Document Type: Article

References (75)

1. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
2. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
3. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
4. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
5. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
6. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
7. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
8. For leading reviews, see: (a) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129. (b) Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683-720. (d) Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316. (e) Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol 10, p 495. (f) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. (g) Sinnot, M. L. Chem. Rev. 1990, 90, 1171. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
9. (a) Carlson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, F. M. J. Biol. Chem. 1993, 268, 570.
10. (b) Taylor, D. L.; Sunkara, P. S.; Liu, P. S.; Kang, M. S.; Bowlin, T. L.; Tyms, A. S. AIDS 1991, 5, 693.
11. (c) Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206.
12. (d) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229.
13. For a review see: Gross, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935.
14. (a) Witczak, Z. J. Carbohydrates as New and Old Targets for Future Drug Design. In Carbohydrates in Drug Design; Witczak, Z. J., Ed.; Marcel Dekker Inc.: New York, 1997; p 1.
15. (b) Balfour, J. A.; McTavish, D. Drugs 1993, 46, 1025.
16. (c) Robinson, K. M.; Begovic, M. E.; Rhinehart, B. L.; Heineke, E. W.; Ducep, J.-B.; Kastner, P. R.; Marshall, F. N.; Danzin, C. Diabetes 1991, 40, 825.
17. (d) Anzeveno, P. B.; Creemer, L. J.; Daniel, J. K.; King, C.-H.; Liu, P. S. J. Org. Chem. 1989, 54, 2539.
18. (e) Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Science 1997, 276, 428.
19. Although the term "azasugar" is widely used in the literature to refer to glycomimetics in which the endocyclic oxygen atom has been replaced by nitrogen, this is not strictly correct according to the IUPAC-IUBM nomenclature recommendations for carbohydrates. "Azahexose" would actually imply that a carbon atom has been exchanged into nitrogen. See: McNaught, A. D. Pure Appl. Chem. 1996, 68, 1919.
20. For reviews on DJ- and DNJ-based inhibitors, see: (a) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340. (b) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
21. For reviews on DJ- and DNJ-based inhibitors, see: (a) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340. (b) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
22. For reviews on DJ- and DNJ-based inhibitors, see: (a) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340. (b) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
23. For reviews on DJ- and DNJ-based inhibitors, see: (a) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340. (b) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
24. For reviews on CS-based inhibitors, see: (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21. (b) Cossy, J.; Vogel, P. In Studies in Natural Products Chemistry; Atta-ur Rahman, Ed.; Elsevier: New York, 1993; Vol. 12, p 275. (c) Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045.
25. For reviews on CS-based inhibitors, see: (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21. (b) Cossy, J.; Vogel, P. In Studies in Natural Products Chemistry; Atta-ur Rahman, Ed.; Elsevier: New York, 1993; Vol. 12, p 275. (c) Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045.
26. For reviews on CS-based inhibitors, see: (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21. (b) Cossy, J.; Vogel, P. In Studies in Natural Products Chemistry; Atta-ur Rahman, Ed.; Elsevier: New York, 1993; Vol. 12, p 275. (c) Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045.
27. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
28. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
29. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
30. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
31. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
32. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
33. The exceptions correspond to compounds having the exocyclic glycosidic oxygen replaced by other atom or group of atoms. Noteworthy examples are aza-C-glycosides and aza-S-glycosides. See: (a) Leewenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5. (b) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R.; J. Am. Chem. Soc. 1997, 119, 4856. (d) Fuchss, T.; Streicher, H.; Schmidt, H. R. Liebigs Ann./Recl. 1997, 1315. (e) Asano, N.; Nishida, M.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 98. (f) Wong, C.-H.; Proveacher, L.; Porco, Jr., J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. (g) Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 4119.
34. For reviews on the reaction mechanism of enzymatic glycosidic bond cleavage, see ref 5f,g and: (a) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (b) White, A.; Rose, D. R. Curr. Opin. Struct. Biol. 1997, 7, 645. (c) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047. (d) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305.
35. For reviews on the reaction mechanism of enzymatic glycosidic bond cleavage, see ref 5f,g and: (a) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (b) White, A.; Rose, D. R. Curr. Opin. Struct. Biol. 1997, 7, 645. (c) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047. (d) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305.
36. For reviews on the reaction mechanism of enzymatic glycosidic bond cleavage, see ref 5f,g and: (a) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (b) White, A.; Rose, D. R. Curr. Opin. Struct. Biol. 1997, 7, 645. (c) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047. (d) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305.
37. For reviews on the reaction mechanism of enzymatic glycosidic bond cleavage, see ref 5f,g and: (a) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (b) White, A.; Rose, D. R. Curr. Opin. Struct. Biol. 1997, 7, 645. (c) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047. (d) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305.
38. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1994, 36, 653.
39. For reviews on the comparative chemical and electronic properties of N-(thio)carbonyl compounds, see: (a) Molina, M. T.; Yáñez, M.; Mó, O.; Notario, R.; Abboud, J.-L. M. The Thiocarbonyl Group. In Supplement A3, The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; Part 2, p 1355. (b) García Fernández, J. M.; Ortiz Mellet, C. Sulfur Rep. 1996, 19, 61. (c) Duus, F. Thiocarbonyl Compounds. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: London, 1979; Vol. 3, p 373. (d) Walter, W.; Voss, J. The Chemistry of Thioamides. In The Chemistry of Amides; Zabicky, J., Ed.; John Wiley & Sons: London, 1970; p 383. (e) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
40. For reviews on the comparative chemical and electronic properties of N-(thio)carbonyl compounds, see: (a) Molina, M. T.; Yáñez, M.; Mó, O.; Notario, R.; Abboud, J.-L. M. The Thiocarbonyl Group. In Supplement A3, The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; Part 2, p 1355. (b) García Fernández, J. M.; Ortiz Mellet, C. Sulfur Rep. 1996, 19, 61. (c) Duus, F. Thiocarbonyl Compounds. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: London, 1979; Vol. 3, p 373. (d) Walter, W.; Voss, J. The Chemistry of Thioamides. In The Chemistry of Amides; Zabicky, J., Ed.; John Wiley & Sons: London, 1970; p 383. (e) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
41. For reviews on the comparative chemical and electronic properties of N-(thio)carbonyl compounds, see: (a) Molina, M. T.; Yáñez, M.; Mó, O.; Notario, R.; Abboud, J.-L. M. The Thiocarbonyl Group. In Supplement A3, The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; Part 2, p 1355. (b) García Fernández, J. M.; Ortiz Mellet, C. Sulfur Rep. 1996, 19, 61. (c) Duus, F. Thiocarbonyl Compounds. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: London, 1979; Vol. 3, p 373. (d) Walter, W.; Voss, J. The Chemistry of Thioamides. In The Chemistry of Amides; Zabicky, J., Ed.; John Wiley & Sons: London, 1970; p 383. (e) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
42. For reviews on the comparative chemical and electronic properties of N-(thio)carbonyl compounds, see: (a) Molina, M. T.; Yáñez, M.; Mó, O.; Notario, R.; Abboud, J.-L. M. The Thiocarbonyl Group. In Supplement A3, The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; Part 2, p 1355. (b) García Fernández, J. M.; Ortiz Mellet, C. Sulfur Rep. 1996, 19, 61. (c) Duus, F. Thiocarbonyl Compounds. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: London, 1979; Vol. 3, p 373. (d) Walter, W.; Voss, J. The Chemistry of Thioamides. In The Chemistry of Amides; Zabicky, J., Ed.; John Wiley & Sons: London, 1970; p 383. (e) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
43. For reviews on the comparative chemical and electronic properties of N-(thio)carbonyl compounds, see: (a) Molina, M. T.; Yáñez, M.; Mó, O.; Notario, R.; Abboud, J.-L. M. The Thiocarbonyl Group. In Supplement A3, The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; Part 2, p 1355. (b) García Fernández, J. M.; Ortiz Mellet, C. Sulfur Rep. 1996, 19, 61. (c) Duus, F. Thiocarbonyl Compounds. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: London, 1979; Vol. 3, p 373. (d) Walter, W.; Voss, J. The Chemistry of Thioamides. In The Chemistry of Amides; Zabicky, J., Ed.; John Wiley & Sons: London, 1970; p 383. (e) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
44. For reviews on the generalized anomeric effect, see: (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. Biochem. 1989, 47, 45. (b) Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995. For recent papers on the controversial subject of the relative contribution of orbitalic and electrostatic interactions to the generalized anomeric effect in azaheterocycles, see: (c) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715. (d) Salzner, U. J. Org. Chem. 1995, 60, 986. (e) Ritter, J.; Gleiter, R.; Irngartinger, H.; Oeser, T. J. Am. Chem. Soc. 1997, 119, 10599.
45. For reviews on the generalized anomeric effect, see: (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. Biochem. 1989, 47, 45. (b) Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995. For recent papers on the controversial subject of the relative contribution of orbitalic and electrostatic interactions to the generalized anomeric effect in azaheterocycles, see: (c) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715. (d) Salzner, U. J. Org. Chem. 1995, 60, 986. (e) Ritter, J.; Gleiter, R.; Irngartinger, H.; Oeser, T. J. Am. Chem. Soc. 1997, 119, 10599.
46. For reviews on the generalized anomeric effect, see: (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. Biochem. 1989, 47, 45. (b) Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995. For recent papers on the controversial subject of the relative contribution of orbitalic and electrostatic interactions to the generalized anomeric effect in azaheterocycles, see: (c) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715. (d) Salzner, U. J. Org. Chem. 1995, 60, 986. (e) Ritter, J.; Gleiter, R.; Irngartinger, H.; Oeser, T. J. Am. Chem. Soc. 1997, 119, 10599.
47. For reviews on the generalized anomeric effect, see: (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. Biochem. 1989, 47, 45. (b) Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995. For recent papers on the controversial subject of the relative contribution of orbitalic and electrostatic interactions to the generalized anomeric effect in azaheterocycles, see: (c) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715. (d) Salzner, U. J. Org. Chem. 1995, 60, 986. (e) Ritter, J.; Gleiter, R.; Irngartinger, H.; Oeser, T. J. Am. Chem. Soc. 1997, 119, 10599.
48. For reviews on the generalized anomeric effect, see: (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. Biochem. 1989, 47, 45. (b) Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995. For recent papers on the controversial subject of the relative contribution of orbitalic and electrostatic interactions to the generalized anomeric effect in azaheterocycles, see: (c) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715. (d) Salzner, U. J. Org. Chem. 1995, 60, 986. (e) Ritter, J.; Gleiter, R.; Irngartinger, H.; Oeser, T. J. Am. Chem. Soc. 1997, 119, 10599.
49. (a) Jiménez Blanco, J. L.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M. Tetrahedron 1998, 54, 14123.
50. (b) Jiménez Blanco, J. L.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M. Chem. Commun. 1998, 2077.
51. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969.
52. Dax, K.; Gaigg, B.; Grassberger, V.; Kölblinger, B.; Stütz, A. E. J. Carbohydr. Chem. 1990, 9, 479.
53. Previous work on the synthesis of 2-thioxo-1,3-O,N-heterocycles from amino sugar templates had shown that β-amino alcohol segments undergo regioselective cyclization to the corresponding oxazolidine-2-thiones upon reaction with thiophosgene, provided that a cis relationship of the reactive groups is allowed. See: (a) García Fernández, J. M.; Ortiz Mellet, C.; Fuentes, J. J. Org. Chem. 1993, 58, 5192. (b) García Fernández, J. M.; Ortiz Mellet, C.; Jiménez Blanco, J. L.; Fuentes, J. J. Org. Chem. 1994, 59, 5565. In the present case, this procedure proved unsatisfactory, affording a rather modest 28% yield. Simultaneous formation of oligomeric material was observed. Using 1,1-thiocarbonyldiimidazole as the thiocarbonylating reagent likewise resulted in low yields.
54. Previous work on the synthesis of 2-thioxo-1,3-O,N-heterocycles from amino sugar templates had shown that β-amino alcohol segments undergo regioselective cyclization to the corresponding oxazolidine-2- thiones upon reaction with thiophosgene, provided that a cis relationship of the reactive groups is allowed. See: (a) García Fernández, J. M.; Ortiz Mellet, C.; Fuentes, J. J. Org. Chem. 1993, 58, 5192. (b) García Fernández, J. M.; Ortiz Mellet, C.; Jiménez Blanco, J. L.; Fuentes, J. J. Org. Chem. 1994, 59, 5565. In the present case, this procedure proved unsatisfactory, affording a rather modest 28% yield. Simultaneous formation of oligomeric material was observed. Using 1,1-thiocarbonyldiimidazole as the thiocarbonylating reagent likewise resulted in low yields.
55. For a review on the synthetic applications of triphosgene, see: Cotarca, L.; Delogu, P.; Nardelli, A., Sunjic, V. Synthesis 1996, 553.
56. 2, proved unsuccessful. When 1,1-carbonyldiimidazole was used as the carbonylating reagent, the corresponding cyclic thiocarbamates were isolated in 50% yield.
57. For clarity of presentation, the authors choose not to use the numbers resulting from the heterocyclic compounds (see the Experimental Section) in the notation of atoms for NMR data. Instead, the notation is kept consistent with the parent carbohydrate compounds. See Figure 1 for atom notation equivalency.
58. (a) Paulsen, H. Annalen 1963, 665, 166.
59. (b) Paulsen, H.; Todt, K. Chem. Ber. 1966, 99, 3450.
60. (c) Rank, W.; Baer, H. H. Carbohydr. Res. 1974, 35, 65.
61. The acetylation/deacetylation step was found to be necessary to avoid extensive formation of 3,6-anhydro derivatives, resulting from intramolecular nucleophilic displacement of the tosylate group by 3-OH.
62. Paulsen, H.; Todt, K. Adv. Carbohydr. Chem. 1968, 23, 115.
63. Humeres, E.; Debacher, N. A.; Sierra, M. M. de S.; Franco, J. D.; Schutz, A. J. Org. Chem. 1998, 63, 1598.
64. Recent theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 4227. (b) Legler, G.; Finken, M.-T. Carbohydr. Res. 1896, 292, 103. (c) Blériot, Y.; Genre-Grandpierre, A.; Imberty, A.; Tellier, C. J. Carbohydr. Chem. 1996, 15, 985. (d) Deng, H.; Chan, A. W.-Y.; Bagdasianan, C. K.; Estupiñán, B.; Ganem, B.; Callender, R. H.; Scharam, V. L. Biochemistry 1996, 35, 6037. (e) Ernert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
65. Recent theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 4227. (b) Legler, G.; Finken, M.-T. Carbohydr. Res. 1896, 292, 103. (c) Blériot, Y.; Genre-Grandpierre, A.; Imberty, A.; Tellier, C. J. Carbohydr. Chem. 1996, 15, 985. (d) Deng, H.; Chan, A. W.-Y.; Bagdasianan, C. K.; Estupiñán, B.; Ganem, B.; Callender, R. H.; Scharam, V. L. Biochemistry 1996, 35, 6037. (e) Ernert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
66. Recent theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 4227. (b) Legler, G.; Finken, M.-T. Carbohydr. Res. 1896, 292, 103. (c) Blériot, Y.; Genre-Grandpierre, A.; Imberty, A.; Tellier, C. J. Carbohydr. Chem. 1996, 15, 985. (d) Deng, H.; Chan, A. W.-Y.; Bagdasianan, C. K.; Estupiñán, B.; Ganem, B.; Callender, R. H.; Scharam, V. L. Biochemistry 1996, 35, 6037. (e) Ernert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
67. Recent theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 4227. (b) Legler, G.; Finken, M.-T. Carbohydr. Res. 1896, 292, 103. (c) Blériot, Y.; Genre-Grandpierre, A.; Imberty, A.; Tellier, C. J. Carbohydr. Chem. 1996, 15, 985. (d) Deng, H.; Chan, A. W.-Y.; Bagdasianan, C. K.; Estupiñán, B.; Ganem, B.; Callender, R. H.; Scharam, V. L. Biochemistry 1996, 35, 6037. (e) Ernert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
68. Recent theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 4227. (b) Legler, G.; Finken, M.-T. Carbohydr. Res. 1896, 292, 103. (c) Blériot, Y.; Genre-Grandpierre, A.; Imberty, A.; Tellier, C. J. Carbohydr. Chem. 1996, 15, 985. (d) Deng, H.; Chan, A. W.-Y.; Bagdasianan, C. K.; Estupiñán, B.; Ganem, B.; Callender, R. H.; Scharam, V. L. Biochemistry 1996, 35, 6037. (e) Ernert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
69. Winchester, B. G.; Cenci di Bello, I.; Richardson, A. C.; Nash, R. J.; Fellows, L. E.; Ramsden, N. G.; Fleet, G. W. J. Biochem. J. 1990, 269, 227.
70. * as integrated in MACROMODEL 6.0 and the GB/SA continuum solvent model for water. The three-dimensional geometries obtained were in agreement with the discussed NMR data.
71. Molyneux, R.-J.; Pan, Y. T.; Tropea, J. E.; Benson, M.; Kaushal, G. P.; Elbein, A. D. Biochemistry 1991, 30, 9981.
72. For the nomenclature used to denote the staggered rotamers about the C-5-C-6 bond in hexopyranoses, see: Bock, K.; Duus, J. Ø. J. Carbohydr. Chem. 1994, 13, 513.
73. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
74. (b) Gobolobov, Yu.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437.
75. Rivera-Sagredo, A.; Cañada, F. J.; Nieto, O.; Jiménez-Barbero, J.; Martín-Lomas, M. Eur. J. Biochem. 1992, 209, 415.