Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5602-5613

  Hinou, Hiroshi ^a,b   Sun, Xue Long ^a,c   Ito, Yukishige ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; OXIDATION; SYNTHESIS (CHEMICAL);

ACCEPTOR MOIETIES;

AROMATIC HYDROCARBONS;

CYTIDINE PHOSPHATE; CYTIDINE PHOSPHATE N ACETYLNEURAMINIC ACID; ENZYME INHIBITOR; LACTOSE; N ACETYLGALACTOSAMINE; SIALIC ACID; SIALYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; ENZYME INHIBITOR INTERACTION; INHIBITION KINETICS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

AMINO SUGARS; CROSS-LINKING REAGENTS; CYTIDINE MONOPHOSPHATE N-ACETYLNEURAMINIC ACID; DIMERIZATION; ENZYME INHIBITORS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR MIMICRY; SIALYLTRANSFERASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037662067     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030042g     Document Type: Article

References (47)

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4. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
5. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
6. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
7. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
8. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
9. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
10. (a) Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174-17181. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397-8406. (c) Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915. (d) Waldscheck, B.; Streiff, M.; Notz, W.; Kinzy, W.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40, 4007-4011. (e) Parang, K.; Till, J. H.; Ablooglu, A. J.; Kohanski, R. A.; Hubbard, S. R.; Cole, P. A. Nature Struct. Biol. 2001, 8, 37-41. (f) Liu, M.; Haddad, J.; Azucena, E,; Kotra, L. P.; Kirzhner, M.; Mobashery, S. J. Org. Chem. 2000, 65, 7422-7431. For a general review, see: Qian, X.; Palcic, M. M. Glycosyltransferase Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; VCH-Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
11. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
12. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
13. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
14. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
15. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
16. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
17. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
18. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
19. Crystal structures of some glycosyltransferases have been reported: β-glucosyltransferase, β-1,4-galactosyltransferase, glucuronyltransferase I, N-acetylglucosaminyltransferase I, and α-1,4-galactosyltransferase have been reported. Glucosyltransferase from phage T4: Vrielink, A.; Ruger, W.; Driessen, H. P. C.; Freemont, P. S. EMBO J. 1994, 13, 3413-3422. SpSA from B. subtilin: Charnock, S. J.; Davies, G. J. Biochemistry 1999, 38, 6380-6385. Bovine β-1,4-galactosyltransferase: Gastinel, L. N.; Cambillau, G.; Bourne, Y. EMBO J. 1999, 18, 3546-3557. MurG from E. coli: Ha, S.; Walker, D.; Shi, Y.; Walker, S. Protein Sci. 2000, 9, 1045-1052. Human glucuronyltransferase I: Pedersen, L. C.; Tsuchida, K.; Kitagawa, H.; Sugahara, K.; Darden, T. A.; Negishi, M. J. Biol. Chem. 2000, 275, 34580-34585. Rabbit N-acetylglucosaminyltransferase I: Ünligil, U. M.; Zhou, S.; Yuwaraj, S.; Sarkar, M.; Schachter, H.; Rini, J. M. EMBO J. 2000, 19, 5269-5280. Bacterial α-1,4-galactosyltransferase: Persson, K.; Ly, H. D.; Dieckelmann, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. J. Nature Struct. Biol. 2001, 8, 166-175. Photoaffinity labeling studies: Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J. Am. Chem. Soc. 1998, 120, 453-454. Hatanaka, Y.; Kempin, U.; Jong-Jip, P. J. Org. Chem. 2000, 65, 5639-5643.
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29. Potent ST inhibitors, which mimic the transition state were reported by Schmidt and co-workers: (a) Müller, B.; Schaub, C.; Schmidt, R. R. Angew. Chem., Int. Ed. 1998, 37, 2893-2897. (b) Amann, F.; Schaub, C.; Müller, B.; Schmidt, R. R. Chem. Eur. J. 1998, 4, 1106-1115. (c) Schwörer, R.; Schmidt, R. R. J. Am. Chem. Soc. 2002, 124, 1632-1637. Toward an antisense approach to ST inhibition, see: Zeng, G.; Li, D. D.; Gao, L.; Birklé, S.; Bieberich, E.; Tokuda, A.; Yu, R. K. Biochemistry, 1999, 38, 8762-8769.
30. Potent ST inhibitors, which mimic the transition state were reported by Schmidt and co-workers: (a) Müller, B.; Schaub, C.; Schmidt, R. R. Angew. Chem., Int. Ed. 1998, 37, 2893-2897. (b) Amann, F.; Schaub, C.; Müller, B.; Schmidt, R. R. Chem. Eur. J. 1998, 4, 1106-1115. (c) Schwörer, R.; Schmidt, R. R. J. Am. Chem. Soc. 2002, 124, 1632-1637. Toward an antisense approach to ST inhibition, see: Zeng, G.; Li, D. D.; Gao, L.; Birklé, S.; Bieberich, E.; Tokuda, A.; Yu, R. K. Biochemistry, 1999, 38, 8762-8769.
31. Potent ST inhibitors, which mimic the transition state were reported by Schmidt and co-workers: (a) Müller, B.; Schaub, C.; Schmidt, R. R. Angew. Chem., Int. Ed. 1998, 37, 2893-2897. (b) Amann, F.; Schaub, C.; Müller, B.; Schmidt, R. R. Chem. Eur. J. 1998, 4, 1106-1115. (c) Schwörer, R.; Schmidt, R. R. J. Am. Chem. Soc. 2002, 124, 1632-1637. Toward an antisense approach to ST inhibition, see: Zeng, G.; Li, D. D.; Gao, L.; Birklé, S.; Bieberich, E.; Tokuda, A.; Yu, R. K. Biochemistry, 1999, 38, 8762-8769.
32. Potent ST inhibitors, which mimic the transition state were reported by Schmidt and co-workers: (a) Müller, B.; Schaub, C.; Schmidt, R. R. Angew. Chem., Int. Ed. 1998, 37, 2893-2897. (b) Amann, F.; Schaub, C.; Müller, B.; Schmidt, R. R. Chem. Eur. J. 1998, 4, 1106-1115. (c) Schwörer, R.; Schmidt, R. R. J. Am. Chem. Soc. 2002, 124, 1632-1637. Toward an antisense approach to ST inhibition, see: Zeng, G.; Li, D. D.; Gao, L.; Birklé, S.; Bieberich, E.; Tokuda, A.; Yu, R. K. Biochemistry, 1999, 38, 8762-8769.
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36. Hinou, H.; Sun, X.-L.; Ito, Y. Tetrahedron Lett. 2002, 43, 9147-9150. Synthesis of bisubstrate analogues of syalyltransferase was announced: M. Izumi, H. Hashimoto et al. XXIst International Carbohydrate Symposium, July 7-12, 2002, Cairns, Australia; PP136.
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40. Separately prepared epoxide 17 (ref 16) gave 3-α-sulfide under identical conditions.
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43. (a) Kajihara's group (Yokohama City University, Japan) reported the enhanced stability of CDP-NeuAc methyl ester (81st Chemical Society of Japan National Meeting, Tokyo, March 2002).
44. (b) Horenstein, B. A.; Bruner, M. J. Am. Chem. Soc. 1998, 118, 10371-10379.
45. ST6N (EC 2.4.99.1), ST3N (EC 2.4.99.5); purchased from Calbiochem-Novabiochem Co.
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47. Sato, K.; Seio, K.; Sekine, M. J. Am. Chem. Soc. 2002, 124, 12715-12724.