Synthesis of S-linked glycopeptides in aqueous solution

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5641-5651

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

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HOMOCYSTEINE;

SODIUM COMPOUNDS; SOLUTIONS; SYNTHESIS (CHEMICAL);

AROMATIC HYDROCARBONS;

BROMINE DERIVATIVE; CYSTEINE; GALACTOSYL BROMIDE; GLUCOSYL BROMIDE; GLYCOPEPTIDE; HOMOCYSTEINE; LACTOSYL BROMIDE; SIALIC ACID DERIVATIVE; SIALYL CHLORIDE; SODIUM CARBONATE; TRIPEPTIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; PEPTIDE SYNTHESIS; PROTEIN GLYCOSYLATION; REACTION ANALYSIS;

CYSTEINE; GLYCOPEPTIDES; GLYCOSYLATION; OLIGOPEPTIDES; SOLUBILITY; SOLUTIONS;

EID: 0037662057     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034148n     Document Type: Article

References (66)

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24. For the synthesis of S-linked glycosyl amino acids, see: (a) Monsigny, M. L. P.; Delay, D.; Vaculik, M. Carbohydr. Res. 1977, 59, 589. (b) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941. (c) Schmidt, R. R.; Stumpp, M. Liebigs Ann. Chem. 1983, 1249. (d) Nicolaou, K. C.; Chucholowski, A.; Polle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155. (e) Elofsson, M.; Walse, B.; Kihberg, J. Tetrahedron Lett. 1991, 32, 7613. (f) Salvador, L. A.; Elofsson, M.; Kihberg, J. Tetrahedron 1995, 51, 5643. (g) Käsbeck, L.; Kessler, H. Liebigs Ann./Recl. 1997, 165. (h) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265. (i) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1289. (j) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405. (k) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995. (l) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636.
25. For the synthesis of S-linked glycosyl amino acids, see: (a) Monsigny, M. L. P.; Delay, D.; Vaculik, M. Carbohydr. Res. 1977, 59, 589. (b) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941. (c) Schmidt, R. R.; Stumpp, M. Liebigs Ann. Chem. 1983, 1249. (d) Nicolaou, K. C.; Chucholowski, A.; Polle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155. (e) Elofsson, M.; Walse, B.; Kihberg, J. Tetrahedron Lett. 1991, 32, 7613. (f) Salvador, L. A.; Elofsson, M.; Kihberg, J. Tetrahedron 1995, 51, 5643. (g) Käsbeck, L.; Kessler, H. Liebigs Ann./Recl. 1997, 165. (h) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265. (i) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1289. (j) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405. (k) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995. (l) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636.
26. For the synthesis of S-linked glycosyl amino acids, see: (a) Monsigny, M. L. P.; Delay, D.; Vaculik, M. Carbohydr. Res. 1977, 59, 589. (b) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941. (c) Schmidt, R. R.; Stumpp, M. Liebigs Ann. Chem. 1983, 1249. (d) Nicolaou, K. C.; Chucholowski, A.; Polle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155. (e) Elofsson, M.; Walse, B.; Kihberg, J. Tetrahedron Lett. 1991, 32, 7613. (f) Salvador, L. A.; Elofsson, M.; Kihberg, J. Tetrahedron 1995, 51, 5643. (g) Käsbeck, L.; Kessler, H. Liebigs Ann./Recl. 1997, 165. (h) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265. (i) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1289. (j) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405. (k) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995. (l) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636.
27. For the synthesis of S-linked glycosyl amino acids, see: (a) Monsigny, M. L. P.; Delay, D.; Vaculik, M. Carbohydr. Res. 1977, 59, 589. (b) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941. (c) Schmidt, R. R.; Stumpp, M. Liebigs Ann. Chem. 1983, 1249. (d) Nicolaou, K. C.; Chucholowski, A.; Polle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155. (e) Elofsson, M.; Walse, B.; Kihberg, J. Tetrahedron Lett. 1991, 32, 7613. (f) Salvador, L. A.; Elofsson, M.; Kihberg, J. Tetrahedron 1995, 51, 5643. (g) Käsbeck, L.; Kessler, H. Liebigs Ann./Recl. 1997, 165. (h) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265. (i) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1289. (j) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405. (k) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995. (l) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636.
28. For the synthesis of S-linked glycosyl amino acids, see: (a) Monsigny, M. L. P.; Delay, D.; Vaculik, M. Carbohydr. Res. 1977, 59, 589. (b) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941. (c) Schmidt, R. R.; Stumpp, M. Liebigs Ann. Chem. 1983, 1249. (d) Nicolaou, K. C.; Chucholowski, A.; Polle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155. (e) Elofsson, M.; Walse, B.; Kihberg, J. Tetrahedron Lett. 1991, 32, 7613. (f) Salvador, L. A.; Elofsson, M.; Kihberg, J. Tetrahedron 1995, 51, 5643. (g) Käsbeck, L.; Kessler, H. Liebigs Ann./Recl. 1997, 165. (h) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265. (i) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1289. (j) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405. (k) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995. (l) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636.
29. For the synthesis of S-linked glycosyl amino acids, see: (a) Monsigny, M. L. P.; Delay, D.; Vaculik, M. Carbohydr. Res. 1977, 59, 589. (b) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941. (c) Schmidt, R. R.; Stumpp, M. Liebigs Ann. Chem. 1983, 1249. (d) Nicolaou, K. C.; Chucholowski, A.; Polle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155. (e) Elofsson, M.; Walse, B.; Kihberg, J. Tetrahedron Lett. 1991, 32, 7613. (f) Salvador, L. A.; Elofsson, M.; Kihberg, J. Tetrahedron 1995, 51, 5643. (g) Käsbeck, L.; Kessler, H. Liebigs Ann./Recl. 1997, 165. (h) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265. (i) Ohnishi, Y.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1289. (j) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405. (k) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995. (l) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636.
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57. An unfavorable hydrogen bond pattern between the acyl-protected (cf. Boc, Z, etc.) NH and the β-OH (or in our case the β-SH) was claimed to be the reason for the reduced reactivity of acyl-protected glycosyl acceptors. See: (a) Szabo, L.; Ramza, J.; Langdon, C.; Polt, R. Carbohydr. Res. 1995, 274, 11. (b) Polt, R.; Szabo, L.; Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249. (c) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309. (d) Yamada, K.; Matsumoto, S.; Nishimura, S. I. J. Chem. Soc., Chem. Commun. 1999, 507. See also refs 13g and 28.
58. An unfavorable hydrogen bond pattern between the acyl-protected (cf. Boc, Z, etc.) NH and the β-OH (or in our case the β-SH) was claimed to be the reason for the reduced reactivity of acyl-protected glycosyl acceptors. See: (a) Szabo, L.; Ramza, J.; Langdon, C.; Polt, R. Carbohydr. Res. 1995, 274, 11. (b) Polt, R.; Szabo, L.; Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249. (c) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309. (d) Yamada, K.; Matsumoto, S.; Nishimura, S. I. J. Chem. Soc., Chem. Commun. 1999, 507. See also refs 13g and 28.
59. An unfavorable hydrogen bond pattern between the acyl-protected (cf. Boc, Z, etc.) NH and the β-OH (or in our case the β-SH) was claimed to be the reason for the reduced reactivity of acyl-protected glycosyl acceptors. See: (a) Szabo, L.; Ramza, J.; Langdon, C.; Polt, R. Carbohydr. Res. 1995, 274, 11. (b) Polt, R.; Szabo, L.; Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249. (c) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309. (d) Yamada, K.; Matsumoto, S.; Nishimura, S. I. J. Chem. Soc., Chem. Commun. 1999, 507. See also refs 13g and 28.
60. An unfavorable hydrogen bond pattern between the acyl-protected (cf. Boc, Z, etc.) NH and the β-OH (or in our case the β-SH) was claimed to be the reason for the reduced reactivity of acyl-protected glycosyl acceptors. See: (a) Szabo, L.; Ramza, J.; Langdon, C.; Polt, R. Carbohydr. Res. 1995, 274, 11. (b) Polt, R.; Szabo, L.; Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249. (c) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309. (d) Yamada, K.; Matsumoto, S.; Nishimura, S. I. J. Chem. Soc., Chem. Commun. 1999, 507. See also refs 13g and 28.
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