C-glycosides of 2-amino-2-deoxy sugars. β-C-glycosides and 1,1-disubstituted variants

Organic Letters

Volumn 6, Issue 14, 2004, Pages 2445-2448

  Liu, Yan ^a   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLYCOSIDE;

ARTICLE; CHEMICAL REACTION; METHYLATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

AMINO SUGARS; CATALYSIS; GLYCOSIDES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SELENIUM; STEREOISOMERISM;

EID: 3242706187     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0491540     Document Type: Article

References (48)

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14. 4 For more recent reports, see: Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479-1483. Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997-999. Dondoni, A.; Mariotti, G.; Marra, A. J. Org. Chem. 2002, 67, 4475-4486. McGarvey, G. J.; Schmidtmann, F. W.; Benedum, T. E.; Kizer, D. E. Tetrahedron Lett. 2003, 44, 3775-3779. Palmier, S.; Vauzeilles, B.; Beau, J. M. Org. Bioorg. Chem. 2003, 1, 1097-1098. Gaurat, O.; Xie, J.; Valery, J. M. J. Carbohydr. Chem. 2003, 22, 645-656. Xie, J. Carbohydr. Res. 2003, 338, 399-406. Miquel, N.; Vignando, S.; Russo, G.; Lay, L. Synlett 2004, 341-343. Wen, X. H.; Hultin, P. G. Tetrahedron Lett. 2004, 45, 1773-1775.
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20. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
21. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
22. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
23. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
24. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
25. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
26. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
27. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
28. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
29. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
30. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
31. For general entries to C(1)-substituted glycals, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Chem. Soc., Chem. Commun. 1986, 925-926. (b) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927. (c) Lesimple, P.; Beau, J. M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201-6204. (d) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821-4823. (e) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120. (f) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262-1272. (g) Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759. (h) Lui, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603. (i) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099. (j) Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723. (k) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754. (l) Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797-1801.
32. The glycal lithiation procedures used have been described previously: Majumder, U.; Cox, J. M.: Rainier, J. D. Org. Lett. 2003, 5, 913-916. Jäkel, C.; Dötz, K. H. J. Organomet. Chem. 2001, 624, 172-185.
33. The glycal lithiation procedures used have been described previously: Majumder, U.; Cox, J. M.: Rainier, J. D. Org. Lett. 2003, 5, 913-916. Jäkel, C.; Dötz, K. H. J. Organomet. Chem. 2001, 624, 172-185.
34. Czernecki, S.; Randriamandimby, D. Tetrahedron Lett. 1993, 34, 7915-7916. Czernecki, S.; Ayadi, E.; Randriamandimby, D. J. Org. Chem. 1994, 59, 8256-8260. Santoyo-González, F.; Calvo-Flores, F. G.; Garcia-Mendoza, P.; Hernández-Mateo, F.: Isac-Garcia, J.; Robles-Díaz, R. J. Org. Chem. 1993, 58, 6122-6125.
35. Czernecki, S.; Randriamandimby, D. Tetrahedron Lett. 1993, 34, 7915-7916. Czernecki, S.; Ayadi, E.; Randriamandimby, D. J. Org. Chem. 1994, 59, 8256-8260. Santoyo-González, F.; Calvo-Flores, F. G.; Garcia-Mendoza, P.; Hernández-Mateo, F.: Isac-Garcia, J.; Robles-Díaz, R. J. Org. Chem. 1993, 58, 6122-6125.
36. Czernecki, S.; Randriamandimby, D. Tetrahedron Lett. 1993, 34, 7915-7916. Czernecki, S.; Ayadi, E.; Randriamandimby, D. J. Org. Chem. 1994, 59, 8256-8260. Santoyo-González, F.; Calvo-Flores, F. G.; Garcia-Mendoza, P.; Hernández-Mateo, F.: Isac-Garcia, J.; Robles-Díaz, R. J. Org. Chem. 1993, 58, 6122-6125.
37. For a discussion of the stereoselectivity of this process and strategies for enhancing gluco selectivity, see: Seeberger, P. H.; Roehrig, S.; Schell, P.; Wang, Y.; Christ, W. J. Carbohydr. Res. 2000, 328, 61-69. As far as we are aware, no study of the azidoselenenation (or related processes) have been reported for C(1)-substituted glycals.
38. 4
39. 1H NMR.
40. For leading references to the stereoselective reduction of anomeric radicals, see: Crich, D.; Lim, L. B. L. J. Chem. Soc., Perkin Trans. 1 1991, 2205-2208. Schmid, W.; Christian, R.; Zbiral, E. Tetrahedron Lett. 1988, 29, 3643-3646. Baumberger, F.; Vasella, A. Helv. Chim. Acta 1983, 66, 2210-2222.
41. For leading references to the stereoselective reduction of anomeric radicals, see: Crich, D.; Lim, L. B. L. J. Chem. Soc., Perkin Trans. 1 1991, 2205-2208. Schmid, W.; Christian, R.; Zbiral, E. Tetrahedron Lett. 1988, 29, 3643-3646. Baumberger, F.; Vasella, A. Helv. Chim. Acta 1983, 66, 2210-2222.
42. For leading references to the stereoselective reduction of anomeric radicals, see: Crich, D.; Lim, L. B. L. J. Chem. Soc., Perkin Trans. 1 1991, 2205-2208. Schmid, W.; Christian, R.; Zbiral, E. Tetrahedron Lett. 1988, 29, 3643-3646. Baumberger, F.; Vasella, A. Helv. Chim. Acta 1983, 66, 2210-2222.
43. 2 of the C(1) substituent, not shown in Figure 1. Similar diagnostic NOE observations were made in the case of C-glycoside 18, as well as C-glycosides 19 and 20 (Scheme 5).
44. Simple O-glycosides (e.g., 1 (R′ = OBn) of 2-amino-2-deoxy sugars act as competitive inhibitors of the glycosylation of GalNAc in vivo. This has significant implications for the expression of mucins and the intracellular trafficking of other glycoproteins. Gouyer, V.; Leteurtre, E.; Zanetta, J. P.; Lesuffleur, T.; Delannoy, P.; Huet, G. Front. Biosci. 2001, 6, D1235-D1244. Huet, G.; Gouyer, V.; Delacour, D.; Richet, C.; Zanetta, J. P.; Delannoy, P.; Degand, P. Biochimie 2003, 85, 323-330. Delacour, D.; Gouyer, V.; Leteurtre, E.; Ait-Slimane, T.; Drobecq, H.; Lenoir, C.; Moreau-Hannedouche, O.; Trugnan, G.; Huet, G. J. Biol. Chem. 2003, 278, 37799-37809.
45. Simple O-glycosides (e.g., 1 (R′ = OBn) of 2-amino-2-deoxy sugars act as competitive inhibitors of the glycosylation of GalNAc in vivo. This has significant implications for the expression of mucins and the intracellular trafficking of other glycoproteins. Gouyer, V.; Leteurtre, E.; Zanetta, J. P.; Lesuffleur, T.; Delannoy, P.; Huet, G. Front. Biosci. 2001, 6, D1235-D1244. Huet, G.; Gouyer, V.; Delacour, D.; Richet, C.; Zanetta, J. P.; Delannoy, P.; Degand, P. Biochimie 2003, 85, 323-330. Delacour, D.; Gouyer, V.; Leteurtre, E.; Ait-Slimane, T.; Drobecq, H.; Lenoir, C.; Moreau-Hannedouche, O.; Trugnan, G.; Huet, G. J. Biol. Chem. 2003, 278, 37799-37809.
46. Simple O-glycosides (e.g., 1 (R′ = OBn) of 2-amino-2-deoxy sugars act as competitive inhibitors of the glycosylation of GalNAc in vivo. This has significant implications for the expression of mucins and the intracellular trafficking of other glycoproteins. Gouyer, V.; Leteurtre, E.; Zanetta, J. P.; Lesuffleur, T.; Delannoy, P.; Huet, G. Front. Biosci. 2001, 6, D1235-D1244. Huet, G.; Gouyer, V.; Delacour, D.; Richet, C.; Zanetta, J. P.; Delannoy, P.; Degand, P. Biochimie 2003, 85, 323-330. Delacour, D.; Gouyer, V.; Leteurtre, E.; Ait-Slimane, T.; Drobecq, H.; Lenoir, C.; Moreau-Hannedouche, O.; Trugnan, G.; Huet, G. J. Biol. Chem. 2003, 278, 37799-37809.
47. (a) Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829-5831.
48. (b) Cui, J. R.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.