Glycomethanethiosulfonates: Powerful reagents for protein glycosylation

Tetrahedron Asymmetry

Volumn 11, Issue 1, 2000, Pages 245-262

  Davis, Benjamin G ^a   Maughan, Michael A T ^a   Green, Martin P ^a   Ullman, Astrid ^b   Jones, J Bryan ^b  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

REAGENT; THIOMESYLIC ACID METHYL ESTER;

ARTICLE; CHROMATOGRAPHY; DEACETYLATION; EGGERTHELLA LENTA; ENZYME KINETICS; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN GLYCOSYLATION; PROTEIN MODIFICATION; REACTION ANALYSIS;

EID: 0034000336     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00497-8     Document Type: Article

References (82)

1. Helenius, A. Mol. Biol. Cell 1994, 5, 253-265.
2. Opdenakker, G.; Rudd, P. M.; Ponting, C. P.; Dwek, R. A. FASEB J. 1993, 7, 1330-1337.
3. Rudd, P. M.; Joao, H. C.; Coghill, E.; Fiten, P.; Saunders, M. R.; Opdenakker, G.; Dwek, R. A. Biochemistry 1994, 33, 17-22.
4. Sharon, N.; Lis, H. Essays in Biochem. 1995, 30, 59-75.
5. (a) Lasky, L. A. Annu. Rev. Biochem. 1995, 64, 113-139.
6. (b) Weis, W. I.; Drickamer, K. Annu. Rev. Biochem. 1996, 65, 441-473.
7. (a) Varki, A. Glycobiology 1993, 3, 97-130.
8. (b) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
9. Simanek, E. E.; Huang, D.-H.; Pasternack, L.; Machajewski, T. D.; Seitz, O.; Millar, D. S.; Dyson, H. J.; Wong, C.-H. J. Am. Chem. Soc. 1998, 120, 11567-11575.
10. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785-838.
11. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
12. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
13. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
14. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
15. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
16. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
17. For reviews, see: (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281. (b) Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic: London, 1994. (c) Abelson, J. N.; Simon., M. I., Eds. Methods Enzymol. 1994, 242. (d) Lee, Y. C.; Lee, R. T., Eds. ibid. 1994, 247. (e) Bill, R. M.; Flitsch, S. F. Chem. Biol. 1996, 3, 145-149. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. (g) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215-3237.
18. (a) Davis, N. J.; Flitsch, S. L. Tetrahedron Lett. 1991, 32, 6793-6796.
19. (b) Wong, S. Y. C.; Guile, G. R.; Dwek, R. A.; Arsequell, G. Biochem. J. 1994, 300, 843-850.
20. (c) Macindoe, W. M.; van Oijen, A. H.; Boons, G.-J. J. Chem. Soc., Chem. Commun. 1998, 847-848.
21. Wynn, R.; Richards, F. M. Methods Enzymol. 1995, 201, 351-356.
22. Standard one-letter amino acid codes are used in this paper, e.g. S=Ser=Serine and L=Leu=Leucine.
23. Molecular Glycobiology; Fukuda, M.; Hindsgaul, O., Eds.; Oxford University Press: Oxford, 1994.
24. (a) Maekawa, K.; Liener, I. E. Arch. Biochem. Biophys. 1960, 91, 108.
25. (b) Longo, M. A.; Combes, D. FEBS Lett. 1995, 375, 63-66.
26. (c) Longo, M. A.; Combes, D. J. Mol. Catal. B 1997, 2, 281-289.
27. (d) Hill, T. G.; Wang, P.; Huston, M. E.; Wartchow, C. A.; Oehler, L. M.; Smith, M. B.; Bednarski, M. D.; Callstrom, M. R. Tetrahedron Lett. 1991, 32, 6823-6826.
28. (e) Wang, P.; Hill, T. G.; Wartchow, C. A.; Huston, M. E.; Oehler, L. M.; Smith, M. B.; Bednarski, M. D.; Callstrom, M. R. J. Am. Chem. Soc. 1992, 114, 378-380.
29. (f) Wartchow, C. A.; Wang, P.; Bednarski, M. D.; Callstrom, M. R. J. Org. Chem. 1992, 60, 2216-2226.
30. (g) Wang, P.; Hill, T. G.; Bednarski, M. D.; Callstrom, M. R. Tetrahedron Lett. 1991, 32, 6827-6830.
31. (h) Davis, B. G.; Lloyd, R. C.; Jones, J. B. J. Org. Chem. 1998, 63, 9614-9615.
32. (i) Davis, B. G.; Lloyd, R. C.; Jones, J. B., submitted for publication, 1999.
33. (j) Lloyd, R. C.; Davis, B. G.; Jones, J. B., submitted for publication, 1999.
34. (k) Baek, W. O.; Vijayalakshmi, M. A. Biochim. Biophys. Acta 1997, 1336, 394-402.
35. Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157-162.
36. Molecular Glycobiology; Fukuda, M.; Hindsgaul, O., Eds.; Oxford University Press: Oxford, 1994.
37. Berglund, P.; DeSantis, G., Stabile, M. R.; Shang, X.; Gold, M.; Bott, R. R.; Graycar, T. P.; Lau, T. H.; Mitchinson, C.; Jones, J. B. J. Am. Chem. Soc. 1997, 119, 5265-5266.
38. Kenyon, G. L.; Bruice, T. W. Methods Enzymol. 1977, 47, 407-430.
39. (a) Douglass, I. B.; Farah, B. S. J. Org. Chem. 1959, 24, 973-975.
40. (b) Levitt, L. S.; Levitt, B. W. J. Org. Chem. 1972, 37, 332-334.
41. (c) Weidner, J. P.; Block, S. S. J. Med. Chem. 1972, 15, 564-567.
42. (d) Palumbo, G.; Caputo, R. Synthesis 1981, 888-890.
43. (e) Block, E.; Zhao, S.-H. J. Org. Chem. 1992, 57, 5815-5817.
44. (f) Billard, T.; Langlois, B. R.; Large, S.; Anker, D.; Roidot, N.; Roure, P. J. Org. Chem. 1996, 61, 7545-7550.
45. (a) Fischer, E.; Delbrück, K. Chem. Ber. 1909, 42, 1476-1482.
46. (b) Schneider, W.; Gille, R.; Eisfeld, K. Chem. Ber. 1928, 61, 1244-1259.
47. (c) Horton, D. Methods Carbohydr. Chem. 1963, 2, 433-437.
48. (d) Cerny, M.; Stanek, J.; Pacak, J. Monatsch. Chem. 1963, 94, 290-294.
49. (e) Apparu, M.; Blanc-Muesser, M.; Defaye, J.; Driguéz, H. Can. J. Chem. 1981, 59, 314-320.
50. Initial approaches to untethered glyco-MTS reagents similar in type to 1,2 were based upon Danishefsky's glycal methodology: Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666. Tris-TBS glucal was prepared according to the method of Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinäy, P. Tetrahedron Lett. 1986, 27, 6201-6204, oxidized to tris-TBS protected 1,2-anhydroglucose using dimethyldioxirane and then reacted with a solution of butylammonium methanethiosulfonate in dichloromethane that had been prepared by ion pair exchange extraction. However, under a variety of conditions and in contrast to the behaviour of other sulfur nucleophiles [see: (a) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361-366. (b) Berkowitz, D. B.; Danishefsky, S. J.; Schultz, G. K. J. Am. Chem. Soc. 1992, 114, 4518-4529], methanethiosulfonate ion failed to open the epoxide moiety of tris-TBS protected 1,2-anhydro-D-glucose.
51. Initial approaches to untethered glyco-MTS reagents similar in type to 1,2 were based upon Danishefsky's glycal methodology: Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666. Tris-TBS glucal was prepared according to the method of Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinäy, P. Tetrahedron Lett. 1986, 27, 6201-6204, oxidized to tris-TBS protected 1,2-anhydroglucose using dimethyldioxirane and then reacted with a solution of butylammonium methanethiosulfonate in dichloromethane that had been prepared by ion pair exchange extraction. However, under a variety of conditions and in contrast to the behaviour of other sulfur nucleophiles [see: (a) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361-366. (b) Berkowitz, D. B.; Danishefsky, S. J.; Schultz, G. K. J. Am. Chem. Soc. 1992, 114, 4518-4529], methanethiosulfonate ion failed to open the epoxide moiety of tris-TBS protected 1,2-anhydro-D-glucose.
52. Initial approaches to untethered glyco-MTS reagents similar in type to 1,2 were based upon Danishefsky's glycal methodology: Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666. Tris-TBS glucal was prepared according to the method of Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinäy, P. Tetrahedron Lett. 1986, 27, 6201-6204, oxidized to tris-TBS protected 1,2-anhydroglucose using dimethyldioxirane and then reacted with a solution of butylammonium methanethiosulfonate in dichloromethane that had been prepared by ion pair exchange extraction. However, under a variety of conditions and in contrast to the behaviour of other sulfur nucleophiles [see: (a) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361-366. (b) Berkowitz, D. B.; Danishefsky, S. J.; Schultz, G. K. J. Am. Chem. Soc. 1992, 114, 4518-4529], methanethiosulfonate ion failed to open the epoxide moiety of tris-TBS protected 1,2-anhydro-D-glucose.
53. Initial approaches to untethered glyco-MTS reagents similar in type to 1,2 were based upon Danishefsky's glycal methodology: Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666. Tris-TBS glucal was prepared according to the method of Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinäy, P. Tetrahedron Lett. 1986, 27, 6201-6204, oxidized to tris-TBS protected 1,2-anhydroglucose using dimethyldioxirane and then reacted with a solution of butylammonium methanethiosulfonate in dichloromethane that had been prepared by ion pair exchange extraction. However, under a variety of conditions and in contrast to the behaviour of other sulfur nucleophiles [see: (a) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361-366. (b) Berkowitz, D. B.; Danishefsky, S. J.; Schultz, G. K. J. Am. Chem. Soc. 1992, 114, 4518-4529], methanethiosulfonate ion failed to open the epoxide moiety of tris-TBS protected 1,2-anhydro-D-glucose.
54. (a) Zemplén, G.; Kunz, A. Ber. Dtsch. Chem. Ges. 1923, 56, 1705-1710.
55. (b) Plattner, J. J.; Gless, R. D.; Rappoport, H. J. Am. Chem. Soc. 1972, 94, 8613-8615.
56. (c) Mori, K.; Sasaki, M. Tetrahedron Lett. 1979, 20, 1329-1332.
57. (d) Herzig, J.; Nudelman, A. Carbohydr. Res. 1986, 153, 162-167.
58. (e) Herzig, J.; Nudelman, A.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 1986, 51, 727-730.
59. (f) Vekemans, J. A. J. M.; Franken, G. A. M.; Chittenden, G. J. F.; Godefroi, E. F. Tetrahedron Lett. 1987, 28, 2299-2300.
60. (g) Cinget, F.; Schmidt, R. R. Synlett 1993, 168-170.
61. Coles, H. W.; Dodds, M. L.; Bergeim, F. H. J. Am. Chem. Soc. 1938, 60, 1020-1022.
62. Dahmén, J.; Frejd, T.; Grönberg, G.; Lave, T.; Magnusson, G.; Noori, G. Carbohydr. Res. 1983, 116, 303-307.
63. Helferich, B.; Lutzmann, H. Justus Liebigs Ann. Chem. 1939, 541, 1-16.
64. Stabile, M. R.; Lai, W. G.; DeSantis, G.; Gold, M.; Jones, J. B.; Mitchinson, C.; Bott, R. R.; Graycar, T. P.; Liu, C.-C. Bioorg. Med. Chem. Lett. 1996, 6, 2501-2512.
65. Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88-95.
66. Hsia, C. Y.; Ganshaw, G.; Paech, C.; Murray, C. J. Anal. Biochem. 1996, 242, 221-227.
67. Plettner, E.; DeSantis, G.; Stabile, M. R.; Jones, J. B. J. Am. Chem. Soc. 1999,121, 4977-4981.
68. Davis, B. G.; Jones, J. B. Synlett 1999, 1495-1507.
69. Ragupathi, G.; Koganty, R. R.; Qiu, D. X.; Lloyd, K. O.; Livingston, P. O. Glycoconjugate J. 1998, 15, 217-221.
70. (a) Leteux, C.; Stoll, M. S.; Childs, R. A.; Chai, W.; Vorozhaikina, M.; Feizi, T. J. Immunol. Methods 1999, 227, 109-119.
71. (b) Leteux, C.; Childs, R. A.; Chai, W. G.; Stoll, M. S.; Kogelberg, H.; Feizi, T. Glycobiology 1998, 8, 227-236.
72. (c) Kichler, A.; Schuber, F. Glycoconjugate J. 1995, 12, 275-281.
73. (d) Kretzschmar, G.; Sprengard, U.; Kunz, H.; Bartnik, E.; Schmidt, W. Tetrahedron 1995, 51, 13015-13030.
74. Prepared from D-glucose according to Scheurer, P. G.; Smith, F. J. Am. Chem. Soc. 1954, 76, 3224.
75. Prepared from the corresponding parent carbohydrates according to the method of Verley, A.; Bölsing, F. Ber. Dtsch. Chem. Ges. 1901, 34, 3354-3358, and purified by flash chromatography.
76. Prepared from lactose according to the method of Hudson, C. S.; Johnson, J. M. J. Am. Chem. Soc. 1915, 37, 1270-1275, and purified by flash chromatography.
77. The synthesis of 4b as an intermediate has been described previously. In our hands this method gave only a poor yield of product. Nagai, K.; Honda, A.; Kiho, T.; Ukai, S.; Tsuchiya, T. Carbohydr. Res. 1989, 190, 165-180.
78. Helferich, B.; Lutzmann, H. Justus Liebigs Ann. Chem. 1939, 541, 1-16.
79. The synthesis of unstable 4e has been described previously. Dahmén, J.; Frejd, T.; Magnusson, G.; Noori, G.; Carlstroem, A. S. Carbohydr. Res. 1984, 125, 237-245.
80. Dahmén, J.; Frejd, T.; Grönberg, G.; Lave, T.; Magnusson, G.; Noori, G. Carbohydr. Res. 1983, 116, 303-307.
81. The use of 4d as a reactant has been described previously, although no details of preparation or characterization were given. Nilsson, K. G. I. U.S. Patent 4 918 009, 1986.
82. Biosym Technologies, Inc. San Diego, CA, USA.