Recent advances in the synthesis of complex N-glycopeptides

Tetrahedron Asymmetry

Volumn 10, Issue 16, 1999, Pages 3045-3094

  Arsequell, G ^a   Valencia, G ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE;

DEGRADATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 0033551876     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00338-9     Document Type: Article

References (348)

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12. Some relevant glycobiology books: (a) Glycopeptides and Related Compounds, Synthesis, Analysis and Applications, D. G. Large, C. D. Warren, Marcel Dekker, New York, 1997; (b) Glycoscience: Synthesis of Oligosaccharides and Glycoconjugates (Topics in Current Chemistry 186); H. Driguez, J. Thiem, Eds., Springer Verlag, Berlin, 1997; (c) Modern Methods in Carbohydrate Synthesis (Frontiers in Natural Product Research Vol. I), S. H. Khan, R. A. O' Neill, Eds., Harwood Academic Publishers, Amsterdam, 1996; (d) Glycoproteins (in New Comprehensive Biochemistry, Vol. 29a, A. Neuberger, L. L. M. Van Deenen, Eds.), J. Montreuil, J. F. G. Vliegenthart, H. Schachter, Eds., Elsevier, Oxford, 1995; (e) Molecular Glycobiology, M. Fukuda, O. Hindsgaul, Eds., IRL Press at Oxford University Press, Oxford, 1994.
13. Some relevant glycobiology books: (a) Glycopeptides and Related Compounds, Synthesis, Analysis and Applications, D. G. Large, C. D. Warren, Marcel Dekker, New York, 1997; (b) Glycoscience: Synthesis of Oligosaccharides and Glycoconjugates (Topics in Current Chemistry 186); H. Driguez, J. Thiem, Eds., Springer Verlag, Berlin, 1997; (c) Modern Methods in Carbohydrate Synthesis (Frontiers in Natural Product Research Vol. I), S. H. Khan, R. A. O' Neill, Eds., Harwood Academic Publishers, Amsterdam, 1996; (d) Glycoproteins (in New Comprehensive Biochemistry, Vol. 29a, A. Neuberger, L. L. M. Van Deenen, Eds.), J. Montreuil, J. F. G. Vliegenthart, H. Schachter, Eds., Elsevier, Oxford, 1995; (e) Molecular Glycobiology, M. Fukuda, O. Hindsgaul, Eds., IRL Press at Oxford University Press, Oxford, 1994.
14. Some relevant glycobiology books: (a) Glycopeptides and Related Compounds, Synthesis, Analysis and Applications, D. G. Large, C. D. Warren, Marcel Dekker, New York, 1997; (b) Glycoscience: Synthesis of Oligosaccharides and Glycoconjugates (Topics in Current Chemistry 186); H. Driguez, J. Thiem, Eds., Springer Verlag, Berlin, 1997; (c) Modern Methods in Carbohydrate Synthesis (Frontiers in Natural Product Research Vol. I), S. H. Khan, R. A. O' Neill, Eds., Harwood Academic Publishers, Amsterdam, 1996; (d) Glycoproteins (in New Comprehensive Biochemistry, Vol. 29a, A. Neuberger, L. L. M. Van Deenen, Eds.), J. Montreuil, J. F. G. Vliegenthart, H. Schachter, Eds., Elsevier, Oxford, 1995; (e) Molecular Glycobiology, M. Fukuda, O. Hindsgaul, Eds., IRL Press at Oxford University Press, Oxford, 1994.
15. Some relevant glycobiology books: (a) Glycopeptides and Related Compounds, Synthesis, Analysis and Applications, D. G. Large, C. D. Warren, Marcel Dekker, New York, 1997; (b) Glycoscience: Synthesis of Oligosaccharides and Glycoconjugates (Topics in Current Chemistry 186); H. Driguez, J. Thiem, Eds., Springer Verlag, Berlin, 1997; (c) Modern Methods in Carbohydrate Synthesis (Frontiers in Natural Product Research Vol. I), S. H. Khan, R. A. O' Neill, Eds., Harwood Academic Publishers, Amsterdam, 1996; (d) Glycoproteins (in New Comprehensive Biochemistry, Vol. 29a, A. Neuberger, L. L. M. Van Deenen, Eds.), J. Montreuil, J. F. G. Vliegenthart, H. Schachter, Eds., Elsevier, Oxford, 1995; (e) Molecular Glycobiology, M. Fukuda, O. Hindsgaul, Eds., IRL Press at Oxford University Press, Oxford, 1994.
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33. A. J. Petrescu, T. D. Butters, G. Reikensmeier, S. Petrescu, F. M. Platt, R. A. Dwek, M. R. Wormald, EMBO J. 1997, 16, 4302.
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45. Some recent reviews, see: (a) R. R. Schmidt, New approaches to glycoconjugate synthesis, Pure Appl. Chem. 1998, 70, 397; (b) C. M. Taylor, Glycopeptides and glycoproteins: focus on the glycosidic linkage, Tetrahedron 1998, 54, 11137 (TR 465); (c) G. J. Boons, R. L. Polt, The chemistry of, O- and, N-linked glycopeptides, Carbohydr. Chem. 1998, 223, G.-J. Boons, Ed., Blackie: London; (d) M. Meldal, P. M. St Hilaire, Synthetic methods of glycopeptide assembly, and biological analysis of glycopeptide products, Curr. Opin. Chem. Biol. 1997, 1, 552; (e) J. Kihlberg, M. Elofsson, L. A. Salvador, Methods Enzymol. 1997, 289, 221; (f) J. Kihlberg, M. Elofsson, Current Med. Chem. 1997, 4, 85.
46. Some recent reviews, see: (a) R. R. Schmidt, New approaches to glycoconjugate synthesis, Pure Appl. Chem. 1998, 70, 397; (b) C. M. Taylor, Glycopeptides and glycoproteins: focus on the glycosidic linkage, Tetrahedron 1998, 54, 11137 (TR 465); (c) G. J. Boons, R. L. Polt, The chemistry of, O- and, N-linked glycopeptides, Carbohydr. Chem. 1998, 223, G.-J. Boons, Ed., Blackie: London; (d) M. Meldal, P. M. St Hilaire, Synthetic methods of glycopeptide assembly, and biological analysis of glycopeptide products, Curr. Opin. Chem. Biol. 1997, 1, 552; (e) J. Kihlberg, M. Elofsson, L. A. Salvador, Methods Enzymol. 1997, 289, 221; (f) J. Kihlberg, M. Elofsson, Current Med. Chem. 1997, 4, 85.
47. Some recent reviews, see: (a) R. R. Schmidt, New approaches to glycoconjugate synthesis, Pure Appl. Chem. 1998, 70, 397; (b) C. M. Taylor, Glycopeptides and glycoproteins: focus on the glycosidic linkage, Tetrahedron 1998, 54, 11137 (TR 465); (c) G. J. Boons, R. L. Polt, The chemistry of, O- and, N-linked glycopeptides, Carbohydr. Chem. 1998, 223, G.-J. Boons, Ed., Blackie: London; (d) M. Meldal, P. M. St Hilaire, Synthetic methods of glycopeptide assembly, and biological analysis of glycopeptide products, Curr. Opin. Chem. Biol. 1997, 1, 552; (e) J. Kihlberg, M. Elofsson, L. A. Salvador, Methods Enzymol. 1997, 289, 221; (f) J. Kihlberg, M. Elofsson, Current Med. Chem. 1997, 4, 85.
48. Some recent reviews, see: (a) R. R. Schmidt, New approaches to glycoconjugate synthesis, Pure Appl. Chem. 1998, 70, 397; (b) C. M. Taylor, Glycopeptides and glycoproteins: focus on the glycosidic linkage, Tetrahedron 1998, 54, 11137 (TR 465); (c) G. J. Boons, R. L. Polt, The chemistry of, O- and, N-linked glycopeptides, Carbohydr. Chem. 1998, 223, G.-J. Boons, Ed., Blackie: London; (d) M. Meldal, P. M. St Hilaire, Synthetic methods of glycopeptide assembly, and biological analysis of glycopeptide products, Curr. Opin. Chem. Biol. 1997, 1, 552; (e) J. Kihlberg, M. Elofsson, L. A. Salvador, Methods Enzymol. 1997, 289, 221; (f) J. Kihlberg, M. Elofsson, Current Med. Chem. 1997, 4, 85.
49. Some recent reviews, see: (a) R. R. Schmidt, New approaches to glycoconjugate synthesis, Pure Appl. Chem. 1998, 70, 397; (b) C. M. Taylor, Glycopeptides and glycoproteins: focus on the glycosidic linkage, Tetrahedron 1998, 54, 11137 (TR 465); (c) G. J. Boons, R. L. Polt, The chemistry of, O- and, N-linked glycopeptides, Carbohydr. Chem. 1998, 223, G.-J. Boons, Ed., Blackie: London; (d) M. Meldal, P. M. St Hilaire, Synthetic methods of glycopeptide assembly, and biological analysis of glycopeptide products, Curr. Opin. Chem. Biol. 1997, 1, 552; (e) J. Kihlberg, M. Elofsson, L. A. Salvador, Methods Enzymol. 1997, 289, 221; (f) J. Kihlberg, M. Elofsson, Current Med. Chem. 1997, 4, 85.
50. Some recent reviews, see: (a) R. R. Schmidt, New approaches to glycoconjugate synthesis, Pure Appl. Chem. 1998, 70, 397; (b) C. M. Taylor, Glycopeptides and glycoproteins: focus on the glycosidic linkage, Tetrahedron 1998, 54, 11137 (TR 465); (c) G. J. Boons, R. L. Polt, The chemistry of, O- and, N-linked glycopeptides, Carbohydr. Chem. 1998, 223, G.-J. Boons, Ed., Blackie: London; (d) M. Meldal, P. M. St Hilaire, Synthetic methods of glycopeptide assembly, and biological analysis of glycopeptide products, Curr. Opin. Chem. Biol. 1997, 1, 552; (e) J. Kihlberg, M. Elofsson, L. A. Salvador, Methods Enzymol. 1997, 289, 221; (f) J. Kihlberg, M. Elofsson, Current Med. Chem. 1997, 4, 85.
51. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
52. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
53. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
54. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
55. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
56. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
57. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
58. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
59. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
60. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
61. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
62. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
63. Past reviews: for chemical synthesis, see: (a) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155; (b) H. Kunz, Angew. Chem., Int. Ed. Engl. 1987, 26, 294; (c) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (d) K. H. Jung, R. R. Schmidt, Curr. Opin. Struct. Biol. 1991, 721; (e) H. Kunz, Pure Appl. Chem. 1993, 65, 1223; (f) O. Kanie, O. Hindsgaul, Curr. Opin. Struct. Biol. 1992, 2, 674; (g) S. Cohen-Anisfeld, P. T. Lansbury Jr., J. Am. Chem. Soc. 1993, 115, 10531; (h) M. Meldal, Curr. Opin. Struc. Biol. 1994, 4, 710; (i) M. Meldal, K. Bock, Glycoconjugate J. 1994, 11, 59; (j) M. Meldal, in Neoglycoconjugates: Preparation and Applications, Y. C. Lee, R. T. Lee, Eds., Academic Press, San Diego, 1994; p. 145; (k) T. Norberg, B. Lüning, J. Tejbrant, Methods Enzymol. 1994, 247, 87; (l) H. G. Garg, K. von dem Bruch, H. Kunz, Adv. Carbohydr. Chem. 1994, 50, 277; for enzymatic synthesis, see: C. H. Wong, M. Schuster, P. Wang, P. Sears, J. Am. Chem. Soc. 1993, 115, 5893.
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113. Some examples: for n-pentenyl glycosyl orthoesters, see: J. G. Allen, B. Fraser-Reid, J. Am. Chem. Soc. 1999, 121, 468; for glycosyl enol ether derivatives, see: Y. Osa, K. Takeda, T. Sato, E. Kaji, Y. Mizuno, H. Takayanagi, Tetrahedron Lett. 1999, 40, 1531; for vinyl glycosides, see: M. Johnson, C. Arles, G.-J. Boons, Tetrahedron Lett. 1998, 39, 9801.
114. Some examples: for n-pentenyl glycosyl orthoesters, see: J. G. Allen, B. Fraser-Reid, J. Am. Chem. Soc. 1999, 121, 468; for glycosyl enol ether derivatives, see: Y. Osa, K. Takeda, T. Sato, E. Kaji, Y. Mizuno, H. Takayanagi, Tetrahedron Lett. 1999, 40, 1531; for vinyl glycosides, see: M. Johnson, C. Arles, G.-J. Boons, Tetrahedron Lett. 1998, 39, 9801.
115. For a review, see: G.-J. Boons, Tetrahedron 1996, 52, 1095 (TR 388). Based on the one-pot chemoselective glycosylation strategy, see: Z. Zhang, I. R. Ollman, X.-Sh. Ye, R. Wischnat, T. Baasov, C.-H. Wong, Programmable one-pot oligosaccharide synthesis, J. Am. Chem. Soc. 1999, 121, 734.
116. For a review, see: G.-J. Boons, Tetrahedron 1996, 52, 1095 (TR 388). Based on the one-pot chemoselective glycosylation strategy, see: Z. Zhang, I. R. Ollman, X.-Sh. Ye, R. Wischnat, T. Baasov, C.-H. Wong, Programmable one-pot oligosaccharide synthesis, J. Am. Chem. Soc. 1999, 121, 734.
117. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
118. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
119. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
120. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
121. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
122. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
123. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
124. For chemical approaches, see: (a) F. Barresi, O. Hindsgaul, in Modern Methods in Carbohydrate Synthesis (Eds. S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, p. 251; (b) T. Limori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415; (c) G. Hodosi, P. Kovàk, J. Am. Chem. Soc. 1997, 119, 2335; (d) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references cited therein; (e) E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121; (f) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1990, 29, 823; (g) H. Paulsen, Angew. Chem., Int. Ed. Engl. 1982, 21, 155. For enzymatic approaches, see: (h) G. Watt, L. Revers, M. C. Webberley, I. B. H. Wilson, S. Flitsch, Angew. Chem., Int. Ed. Engl. 1997, 36, 2354; (i) J. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem. 1993, 12, 651; (j) S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993.
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