A concise methodology for the stereoselective synthesis of O- glycosylated amino acid building blocks: Complete 1H NMR assignments and their application in solid-phase glycopeptide synthesis

Journal of Peptide Research

Volumn 52, Issue 3, 1998, Pages 165-179

  Satyanarayana, J ^a   Gururaja, T L ^a   Naganagowda, G A ^a   Ramasubbu, N ^a   Levine, M J ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

1H NMR; Conformation; O linked glycopeptides; O glycosylated amino acids; Salivary mucin; Solid phase peptide synthesis (SPPS); Stereoselective synthesis

Indexed keywords

AMINO ACID; GLYCOPEPTIDE; MUCIN; SYNTHETIC PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; GLYCOSYLATION; HUMAN; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0031684915     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1998.tb01473.x     Document Type: Article

References (90)

1. Rademacher, T.W., Parekh, R.B. & Dwek, R.A. (1988) Annu. Rev. Biochem. 57, 785-838.
2. Kornfeld, R. & Kornfeld, S. (1985) Annu. Rev. Biochem. 54, 631-664.
3. Shakin-Eshleman, S.H. & Spitalnik, S.L. (1993) Trends Glycosci. Glycotechnol. 5, 355-368.
4. Schachter, H. & Brockhausen, I. (1992) in Glycoconjugates: Composition, Structure and Function (Allen, H.J., Kisailus, E.C., eds.), pp. 263-332, Marcel Dekker, New York.
5. Strous, G.J. & Dekker, J. (1992) Crit. Rev. Biochem. Mol. Biol. 27, 57-92.
6. Carraway, K.L. & Hull, S.R. (1991) Glycobiology 1, 131-138.
7. Varki, A. (1993) Glycobiology 3, 97-130.
8. Lis, H. & Sharon, N. (1993) Eur. J. Biochem. 218, 1-27.
9. Wyss, D.F., Choi, J.S., Li, J., Knoppers, M.H., Willis, K.J., Arulanasdam, A.R.N., Smolyar, A., Reinherz, E.L. & Wager, G. (1995) Science 269, 1273-1278.
10. Live, D.H., Kumar, R.A., Beebe, X. & Danishefsky, S.J. (1996) Proc. Natl. Acad. Sci. USA 93, 12759-12761.
11. O'Connor, S.E. & Imperiali, B. (1997) J. Am. Chem. Soc. 119, 2295-2296.
12. Kunz, H. (1987) Angew. Chem. Int. Ed. Engl. 26, 294-308.
13. Paulsen, H. (1990) Angew. Chem. Int. Ed. Engl. 29, 823-938.
14. Polt, R., Szabo, L., Treiberg, J., Li, Y. & Hruby, V.J. (1992) J. Am. Chem. Soc. 114, 10249-10258.
15. Halcomb, R.L. & Wong, C.-H. (1995) Curr. Opin. Struct. Biol. 3, 694-700.
16. Meldal, M. & Bock, K. (1994) Glycoconj. J. 11, 59-63.
17. Meldal., M. (1994) in Neoglycoconjugates (Lee, Y.C., Lee, R.T., eds.), pp. 145-198, Academic Press, San Diego, CA.
18. Norberg, T., Lung, B. & Tejbrant, J. (1994) Methods Enzymol. 247, 87-106.
19. Danishefsky, S.J. & Roberge, J.Y. (1996) in Glycopeptides and Related Compounds: Chemical Synthesis, Analysis and Applications (Large, D.G., Warren, C.D., eds.), pp. 245-294, Marcel Dekker, New York.
20. Meinjohanns, E., Meldal, M., Schleyer, A., Paulsen, H. & Bock, K. (1996) J. Chem. Soc. Perkin Trans. 1 985-993.
21. Qiu, D., Gandhi, S.S. & Koganty, R.R. (1996) Tetrahedron Lett. 37, 595-598.
22. Nakara, Y., Iijima, H. & Ogawa, T. (1996) in Modern Methods in Carbohydrate Synthesis (Khan, S.H., O'Neill, R.A., eds.), pp. 301-315, Harwood Academic Publishers, Reading, Berks, England.
23. Rademann, J. & Schmidt, R.R. (1995) Carbohydr. Res. 269, 217-225.
24. Elofsson, M. & Kihlberg, J. (1995) Tetrahedron Lett. 36, 7499-7502.
25. Seitz, O. & Kunz, H. (1995) Angew. Chem. Int. Ed. Engl. 34, 803-805.
26. Peters, S., Bielfeldt, T., Meldal, M., Bock, K. & Paulsen, H. (1992) J. Chem. Soc. Perkin Trans. 1 1163-1171.
27. Luning, B., Norberg, T. & Tejbrant, J. (1989) Glycoconj. J. 6, 5-19.
28. Wakabayashi, K. & Pigman, W. (1974) Carbohydr. Res. 35, 3-14.
29. Derevitskaya, V.A., Vafina, M.G. & Kochetkov, N.K. (1967) Carbohydr. Res. 3, 377-388.
30. Jones, J.K.N., Perry, M.B., Shelton, B. & Walton, D.J. (1961) Can. J. Chem. 39, 1005-1016.
31. Paulsen, H. & Holck, J.-P. (1982) Carbohydr. Res. 109, 89-107.
32. Ferrari, B. & Pavia, A.A. (1980) Carbohydr. Res. 79, C1-C7.
33. Kaifu, R. & Osawa, T. (1979) Carbohydr. Res. 69, 79-88.
34. Paulsen, H., Peters, S., Bielfeldt, T., Meldal, M. & Bock, K. (1995) Carbohydr. Res. 268, 17-34.
35. Sazabo, L., Ramza, J., Langdon, C. & Polt, R. (1995) Carbohydr. Res. 274, 11-28.
36. Garg, H.G. & Jeanloz, R.W. (1976) Carbohydr. Res. 49, 482-488.
37. Lacombe, J.M. & Pavia, A.A. (1983) J. Org. Chem. 48, 2557-2563.
38. Garegg, P.J. & Norberg, T. (1976) Carbohydr. Res. 52, 235-240.
39. Lacombe, J.M., Pavia, A.A. & Rocheville, J.M. (1981) Can. J. Chem. 59, 473-481.
40. Higashi, K., Nakayama, K., Soga, T., Kouichi, U. & Kusama, T. (1990) Chem. Pharm. Bull. 38, 3280-3282.
41. Paulsen, H., Bielfeldt, T., Peters, S., Meldal, M. & Bock, K. (1994) Liebigs Ann. Chem. 369-379.
42. Paulsen, H. & Paal, M. (1984) Carbohydr. Res. 135, 71-84.
43. Bobek, L.A., Tsai, H., Biesbrock, A.R. & Levine, M.J. (1993) J. Biol. Chem. 268, 20563-20569.
44. Reddy, M.S., Bobek, L.A., Haraszthy, G.G., Biesbrock, A.R. & Levine, M.J. (1992) Biochem. J. 287, 639-643.
45. Schenkels, L.C.P.M., Gururaja, T.L. & Levine, M.J. (1996) in Oral Mucosal Drug Delivery (Rathbone, M.J., ed.), pp. 191-220, Marcel Dekker, New York.
46. Levine, M.J. (1993) Ann. N.Y. Acad. Sci. 694, 11-16.
47. Fields, G.B. & Noble, R.L. (1990) Int. J. Pept. Protein Res. 35, 161-214.
48. Hudson, D. (1988) J. Org. Chem. 53, 617-624.
49. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P.I. (1970) Anal. Biochem. 34, 595-598.
50. Meldal, M., Bielfeldt, T., Peters, S., Jensen, K.J., Paulsen, H. & Bock K. (1994) Int. J. Pept. Protein Res. 43, 529-236.
51. Gururaja, T.L., Ramasubbu, N. & Levine, M.J. (1996) Lett. Pept. Sci. 3, 79-88.
52. Gururaja, T.L. & Levine, M.J. (1996) Pept. Res. 6, 283-289.
53. Piantini, U., Sorensen, O.W. & Ernst, R.R. (1982) J. Am. Chem. Soc. 104, 6800-6801.
54. States, D.J., Haberkorn, R.A. & Rubin, D.J. (1982) J. Magn. Reson. 48, 286-292.
55. Jeener, J., Meier, B.H., Bachmann, P. & Ernst, R.R. (1979) J. Chem. Phys. 71, 4546-4553.
56. Kumar, A., Ernst, R.R. & Wuthrich, K. (1980) Biochem. Biophys. Res. Commun. 95, 1-6.
57. Rance, M., Bodenhausen, G., Wagner, G., Wuthrich, K. & Ernst, R.R. (1985) J. Magn. Reson. 62, 497-510.
58. Wuthrich, K. (1986) NMR of Proteins and Nucleic Acids, John Wiley, New York.
59. Paulsen, H. & Paal, M. (1984) Carbohydr. Res. 135, 53-69.
60. Sabesan, S. & Lemieux, R.U. (1984) Can. J. Chem. 62, 644-654.
61. Ferrier, R.J. & Rurneaux, R.H. (1976) Carbohydr. Res. 52, 63-68.
62. Schon, I. & Kisfaludy, L. (1986) Synthesis 303-305.
63. Vargas-Berenguel, A., Meldal, M., Paulsen, H. & Bock, K. (1994) J. Chem. Soc. Perkin Trans. 1 2615-2619.
64. Urge, L., Otvos Jr., L., Lang, E., Wroblewski, K., Laczko, I. & Hollosi, M. (1991) Carbohydr. Res. 235, 83-93.
65. Reimer, K.B., Meldal, M., Kusumoto, S., Fukase, K. & Bock, K. (1993) J. Chem. Soc. Perkin Trans. 1 925-932.
66. Haltiwanger, R.S., Kelly, W.G., Roquemore, E.P., Blomberg, M.A., Dong, D.L.Y., Kreppel, L., Chou, T.Y. & Hart, G.W. (1992) Biochem. Soc. Trans. 20, 264-269.
67. Dong, D.L.-Y., Xu, Z.-S., Chevrier, M.R., Cotter, R.J., Cleveland, D.W. & Hart, G.W. (1993) J. Biol. Chem. 268, 16679-16687.
68. Germain, R.N. (1995) Ann. N.Y. Acad. Sci. 754, 114-125.
69. Haurum, J.S., Tan, L., Arsequell, G., Frodsham, P., Lellouch, A.C., Moss, P.A., Dwek, R.A., McMichael, A.J. & Elliott, T. (1995) Eur. J. Immunol. 25, 3270-3276.
70. Gururaja, T.L., Ramasubbu, N., Paloth, V., Reddy, M.S., Ramalingam, K. & Levine, M.J. (1998) Glycoconj. J. (in press).
71. O'Connell, B.C., Hagen, F.K. & Tabak, L.A. (1992) J. Biol. Chem. 267, 25010-25018.
72. Nehrke, K., Hagen, F.K. & Tabak, L.A. (1996) J. Biol. Chem. 271, 7061-7065.
73. Elhammer, A.P., Poorman, R.A., Brown, E., Maggiora, L.L., Hoogerheide, J.G. & Kezdy, F.J. (1993) J. Biol. Chem. 268, 10029-10038.
74. Hansen, J.E., Lund, O., Engelbrecht, J., Bohr, H., Nielsen, J.O., Hansen J.-E.S. & Brunak, S. (1995) Biochem. J. 308, 801-813.
75. Atherton, E., Holder, J.L., Meldal, M., Sheppard, R.C. & Valerio, R.M. (1988) J. Chem. Soc. Perkin Trans. 1 2887-2894.
76. Dryland, A. & Sheppard, R.C. (1988) Tetrahedron 44, 859-876.
77. Paulsen, H., Schleyer, A., Mathieux, N., Meldal, M. & Bock, K. (1997) J. Chem. Soc. Perkin Trans. 1 281-293.
78. Ronish, E.W. & Krimm, S. (1974) Biopolymers 13, 1635-1651.
79. Woody, R.W. (1977) J. Polymer Sci. 12, 181-321.
80. MacArthur, M.W. & Thornton, J.M. (1991) J. Mol. Biol. 218, 397-412.
81. Sreerama, N. & Woody, R.W. (1994) Biochemistry 33, 10022-10025.
82. Vijaykumar, E.K.S., Sudha, T.S. & Balaram, P. (1984) Biopolymers 23, 877-886.
83. Raj, P.A., Marcus, E. & Edgerton, M. (1996) Biochemistry 35, 4314-4325.
84. Montreuil, J. (1980) Adv. Carbohydr. Chem. Biochem. 37, 157-223.
85. Liu, X., Sejbal, J., Kotovych, G., Koganty, R.R., Reddish, M.A., Jackson, L., Gandhi, S.S., Mendonca, A.J. & Longenecker, B.M. (1995) Glycoconj. J. 12, 607-617.
86. Arsequell, G., Haurum, J.S., Elliot, T., Dwek, R.A. & Lellouch, A.C. (1995) J. Chem. Soc. Perkin Trans. 1 1739-1745.
87. Butenhof, K.J. & Gerken, T.A. (1993) Biochemistry 32, 2650-2663.
88. Mimura, Y., Inoue, Y., Maeji, N.J. & Chujo, R. (1992) Int. J. Biol. Macromol. 14, 242-248.
89. Shogren, R., Gerken, T.A. & Jentoft, N. (1989) Biochemistry 28, 5525-5535.
90. Liang, R., Andreotti, A.H. & Kahne, D (1995) J. Am. Chem. Soc. 117, 10395-10396.