Development of Co- and post-translational synthetic strategies to C-neoglycopeptides

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3591-3594

  McGarvey, Glenn J ^a   Benedum, Tyler E ^a   Schmidtmann, Frank W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE;

ARTICLE; CHEMISTRY; PROTEIN CONFORMATION; PROTEIN PROCESSING; SYNTHESIS;

GLYCOPEPTIDES; PROTEIN CONFORMATION; PROTEIN PROCESSING, POST-TRANSLATIONAL;

EID: 0037126261     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0264861     Document Type: Article

References (33)

1. For reviews addressing cell surface carbohydrates, see: (a) Cell Surface and Extracellular Glycoconjugate; Roberts, D. D., Mecham, R. P., Eds.; Academic Press: New York, 1993.
2. (b) Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701-710.
3. (c) Hakomori, S.-i. Biochem. Soc. Trans. 1993, 21, 583-595.
4. (d) Hakomori, S.-i.; Igarashi, Y. J. Biochem. 1995, 118, 1091-1103.
5. (e) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2755-2794.
6. (f) Hollenbaugh, D.; Bajorath, J.; Aruffo, A. In Bioorganic Chemistry: Carbohydrates; Hecht, S., Ed.; Oxford University Press: New York, 1999; Chapter 8, pp 313-334.
7. For reviews in this area see: (a) Glycoproteins and Disease; Montreuil, J., Vliegenthart, J. F. G., Schachter, H., Eds.; Elsevier: New York, 1996.
8. (b) Glycoproteins and Human Disease; Brockhausen, I., Kuhns, W., Eds.; Chapman and Hall: New York, 1997.
9. (c) Brockhausen, I.; Schutzbach, J.; Kuhns, W. Acta Anat. 1998, 161, 36-78.
10. For reviews on glycopeptide synthesis see: (a) Davis, B. G. Chem. Rev. 2002, 102, 579-601.
11. (b) Seitz, O. Chembiochem 2000, 1, 214-246.
12. (c) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
13. Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1997, 8, 2839-2876.
14. (a) Tsuda, T.; Nishimura, S.-I. Chem. Commun. 1996, 2779-2780.
15. (b) Cohen-Anisfeld, S.; Lansbury, P. T., Jr. J. Am. Chem. Soc. 1993, 115, 10531-10537.
16. (c) Paulsen, H.; Scheyer, A.; Nathieux, N.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1997, 281-293.
17. (d) Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587-1595.
18. (e) Grandjean, C.; Gras-Masse, H.; Melnyk, O. Chem. Eur. 2001, 7, 230-239.
19. (f) Hang, H. C.; Bertozzi, C. R. Acc. Chem. Res. 2001, 34, 727-736.
20. For reviews of olefin metathesis applied to carbohydrate chemistry see: (a) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
21. (b) Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stutz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588.
22. For a review on C-neoglycopeptides, see: Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4421.
23. For related studies see: (a) Dominique, R.; Liu, B.; Das, S. K.; Roy, R. Synthesis 2000, 862-868.
24. (b) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380-2388.
25. Ciu, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
26. The advantage of early, unambiguous establishment of anomeric stereochemistry has been noted previously: Chen, X. T.; Sames, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 7760-7769.
27. (a) For the Fmoc protected form see: Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung J. Am. Chem. Soc. 1997, 119, 6656-673.
28. (b) For the Boc protected form see: Myers, A. G.; Gleason, J. L. Org. Synth. 1999, 76, 57-76.
29. All the starting materials were consumed in this reaction to afford a mixture of the three possible metathesis products (1 cross + 2 self-metathesis products). It is important to note that participation of these products in further metathesis reactions is insignificant under these reaction conditions. This will be reported in due course.
30. Oltvoort, J. J.; van Boeckel, C. A. A.; de Koning, J. H.; van Boom, J. H. Synthesis 1981, 305-308.
31. Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482.
32. That only a very modest improvement in yield is observed with 12 relative to 11 is consistent with the noticeably lower reactivity of the lactose substrates.
33. See Supporting Information for the synthesis of tripeptide 15.