Synthesis of α-S-linked glycopeptides in water containing solution

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6063-6067

  Zhu, Xiangming ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; BETA BROMOALANINE; GLYCOPEPTIDE; N ACETYLGALACTOSAMINE; N ACETYLGLUCOSAMINE; PEPTIDE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PH;

EID: 0037629657     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01465-5     Document Type: Article

References (36)

1. Grogan M.J., Pratt M.R., Marcaurelle L.A., Bertozzi C.R. Annu. Rev. Biochem. 71:2002;593-634.
2. For some recent reviews on glycopeptide synthesis, see: (a) Jansson, A. M.; Hilaire, P. M. S.; Meldal, M. In Synthesis of Peptides and Peptidomemetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Houben-Weyl: Stuttgart, 2003; p. 235; (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601; (c) Wittmann, V. In Glycoscience: Glycoproteins; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; p. 2253; (d) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537; (e) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045-3094; (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
3. For some recent reviews on glycopeptide synthesis, see: (a) Jansson, A. M.; Hilaire, P. M. S.; Meldal, M. In Synthesis of Peptides and Peptidomemetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Houben-Weyl: Stuttgart, 2003; p. 235; (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601; (c) Wittmann, V. In Glycoscience: Glycoproteins; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; p. 2253; (d) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537; (e) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045-3094; (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
4. For some recent reviews on glycopeptide synthesis, see: (a) Jansson, A. M.; Hilaire, P. M. S.; Meldal, M. In Synthesis of Peptides and Peptidomemetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Houben-Weyl: Stuttgart, 2003; p. 235; (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601; (c) Wittmann, V. In Glycoscience: Glycoproteins; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; p. 2253; (d) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537; (e) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045-3094; (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
5. For some recent reviews on glycopeptide synthesis, see: (a) Jansson, A. M.; Hilaire, P. M. S.; Meldal, M. In Synthesis of Peptides and Peptidomemetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Houben-Weyl: Stuttgart, 2003; p. 235; (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601; (c) Wittmann, V. In Glycoscience: Glycoproteins; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; p. 2253; (d) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537; (e) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045-3094; (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
6. For some recent reviews on glycopeptide synthesis, see: (a) Jansson, A. M.; Hilaire, P. M. S.; Meldal, M. In Synthesis of Peptides and Peptidomemetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Houben-Weyl: Stuttgart, 2003; p. 235; (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601; (c) Wittmann, V. In Glycoscience: Glycoproteins; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; p. 2253; (d) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537; (e) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045-3094; (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
7. For some recent reviews on glycopeptide synthesis, see: (a) Jansson, A. M.; Hilaire, P. M. S.; Meldal, M. In Synthesis of Peptides and Peptidomemetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Houben-Weyl: Stuttgart, 2003; p. 235; (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601; (c) Wittmann, V. In Glycoscience: Glycoproteins; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; p. 2253; (d) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537; (e) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045-3094; (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
8. For more recent work on glycopeptide and glycoprotein mimetics, see: Ranandet, O.; Dumy, P. Org. Lett. 2003, 5, 243-246; Liu, H.; Wang, L.; Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 1702-1703 and references cited therein.
9. For more recent work on glycopeptide and glycoprotein mimetics, see: Ranandet, O.; Dumy, P. Org. Lett. 2003, 5, 243-246; Liu, H.; Wang, L.; Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 1702-1703 and references cited therein.
10. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390.
11. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
12. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
13. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
14. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
15. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
16. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
17. For the synthesis of S-linked glycopeptides or S-linked neoglycopeptides, see: (a) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271; (b) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192; (c) Michael, K.; Wittmann, V.; Knig, W.; Sandow, J.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 59-70; (d) Elofsson, M.; Walse, B.; Kihlberg, J. Tetrahedron Lett. 1991, 32, 7613-7616; (e) Malkinson, J. P.; Falconer, R. A. Tetrahedron Lett. 2002, 43, 9549-9552; (f) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541; (g) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2002, 12, 997.
18. Zhu, X.; Pachamuthu, K.; Schmidt, R. R. J. Org. Chem. in print.
19. Horton D., Wander J.D. Pigman W.W., Horton D. Carbohydrates: Chemistry and Biochemistry. 4B:1990;799 Academic Press, New York.
20. Driguez H. ChemBioChem. 2:2001;311-318.
21. McGarvey G.J., Benedum T.E., Schmidtmann F.W. Org. Lett. 4:2002;3591-3594. and references cited therein.
22. Kunz H., Lohr B., Habermann J. Finch P. Carbohydrates: Structures, Synthesis and Dynamics. 1999;187 Kluwer Academic Publishers, Dordrecht.
23. Winterfeld G.A., Ito Y., Ogawa T., Schmidt R.R. Eur. J. Org. Chem. 5:1999;1167-1171.
24. For the synthesis of α-S-linked glycosyl amino acids, see: (a) Käsbeck, L.; Kessler, H. Liebigs Ann./Recueil 1997, 165-167; (b) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (c) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636-3638; (d) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
25. For the synthesis of α-S-linked glycosyl amino acids, see: (a) Käsbeck, L.; Kessler, H. Liebigs Ann./Recueil 1997, 165-167; (b) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (c) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636-3638; (d) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
26. For the synthesis of α-S-linked glycosyl amino acids, see: (a) Käsbeck, L.; Kessler, H. Liebigs Ann./Recueil 1997, 165-167; (b) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (c) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636-3638; (d) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
27. For the synthesis of α-S-linked glycosyl amino acids, see: (a) Käsbeck, L.; Kessler, H. Liebigs Ann./Recueil 1997, 165-167; (b) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (c) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636-3638; (d) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
28. Barton D.H.R., Herve Y., Potier P., Thierry J. Tetrahedron. 44:1988;5479.
29. Salituro G.M., Townsend C.A. J. Am. Chem. Soc. 112:1990;760-770.
30. Ohnishi Y., Ichikawa M., Ichikawa Y. Bioorg. Med. Chem. Lett. 10:2000;1289-1291.
31. Stocking E.M., Schwarz J.N., Senn H., Salzmann M., Silks L.A. J. Chem. Soc., Perkin Trans. 1. 1997;2443-2447.
32. Zhu, X., unpublished results.
33. Carrasco M.R., Nguyen M.J., Burneu D.R., MacLaren M.D., Hengel S.M. Tetrahedron Lett. 43:2002;5727-5729.
34. 4, concentrated in vacuo to give a residue which was purified by flash column chromatography to afford the corresponding thioglycoside.
35. 14S (802.9): C, 53.85; H, 7.28; N, 6.98. Found: C, 53.64; H, 7.49; N, 6.51.
36. +).