Synthesis of novel S-neoglycopeptides from glycosylthiomethyl derivatives

Organic Letters

Volumn 6, Issue 7, 2004, Pages 1083-1085

  Zhu, Xiangming ^a   Pachamuthu, Kandasamy ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; ASPARTIC ACID; GLUTAMIC ACID; METHYL GROUP; PEPTIDASE; PEPTIDE; S NEOGLYCOPEPTIDASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 2342644680     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036186z     Document Type: Article

References (48)

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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; pp 235-332. (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; pp 2253-2352. (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; pp 235-332. (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; pp 2253-2352. (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 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; pp 235-332. (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; pp 2253-2352. (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.
9. 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; pp 235-332. (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; pp 2253-2352. (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.
10. 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; pp 235-332. (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; pp 2253-2352. (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.
11. Reviewed in: (a) Hang, H. C.; Bertozzi, C. R. Acc. Chem. Res. 2001, 34, 727-736. (b) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390.
12. Reviewed in: (a) Hang, H. C.; Bertozzi, C. R. Acc. Chem. Res. 2001, 34, 727-736. (b) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390.
13. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
14. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
15. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
16. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
17. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
18. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
19. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
20. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
21. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
22. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. (i) Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
23. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. (i) Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
24. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. (i) Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
25. There are a large number of reports on the synthesis of neoglycopeptides; for some recent examples, see: (a) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420. (b) Macindoe, W. M.; van Oijen, A. H.; Boons, G. J. Chem. Commun. 1998, 847-848. (c) Peri, F.; Cipolla, L.; Ferla, B. L.; Dumy, P.; Nicotra, F. Glycoconjugate J. 1999, 16, 399-404. (d) Wittmann, V.; Seeberger, S. Angew. Chem. 2000, 112, 4508-4512; Angew. Chem., Int. Ed. 2000, 39, 4348-4352. (e) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125. (f) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087. (g) Ramos, D.; Rollin, P.; Klaffke, W. J. Org. Chem. 2001, 66, 2948-2956. (h) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein. (i) Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594. (k) Filira, F.; Biondi, B.; Biondi, L.: Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063. (l) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
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39. The yields in Scheme 1 were based on recovered starting materials; for details, see the Experimental Section (Supporting Information).
40. (a) Mitin, Y. V.; Zapevalova, N. P. Int. J. Peptide Protein Res. 1990, 35, 352-356.
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43. All the glycosylthiols used here were prepared according to a known procedure: Cerný, M.; Vrkoč, J.; Staněk, J. Collect. Czech. Chem. Commun. 1959, 24, 64-69.
44. Presumably, polymerization took place in this reaction, giving rise to several byproducts as indicated by TLC.
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48. (a) In view of the distance between the sugar and the peptide backbone, compounds 8 and 28 could be good mimetics of native N-glycopeptides.