An efficient Mitsunobu protocol for the one-pot synthesis of S-glycosyl amino-acid building blocks and their use in combinatorial spot synthesis of glycopeptide libraries

Nature Protocols

Volumn 1, Issue 4, 2006, Pages 1987-1994

  Ziegler, Thomas ^a   Schips, Carsten ^b  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE; GLYCOSYLATED BETA PROTEIN; GLYCOSYLATED PROTEIN; LECTIN; OLIGOSACCHARIDE; PEPTIDE LIBRARY; PEROXIDASE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; COMBINATORIAL CHEMISTRY; COMBINATORIAL LIBRARY; COMPLEX FORMATION; CONTROLLED STUDY; MITSUNOBU REACTION; MOLECULAR MIMICRY; NONHUMAN; ONE POT SYNTHESIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN GLYCOSYLATION;

AMINO ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; GLYCOPEPTIDES; GLYCOSYLATION; PEPTIDE LIBRARY;

EID: 34248655133     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2006.307     Document Type: Article

References (11)

1. Sharon, N. & Lis, H. Lectins as cell recognition molecules. Science 246, 227-234 (1989).
2. Seitz, O. Glycopeptide synthesis and the effects of glycosylation on protein structure and activity. ChemBioChem 1, 214-246 (2000).
3. Sampson, N.S., Mrksich, M. & Bertozzi, R.C. Surface molecular recognition. Proc. Natl. Acad. Sci. USA 98, 12870-12871 (2001).
4. Rudd, P.M., Elliott, T., Cresswell, P., Wilson, I.A. & Dwek, R.A. Glycosylation and the immune system. Science 291, 2370-2376 (2001).
5. Crocker, P.R. Mammalian Carbohydrate Recognition Systems 1-249 (Springer, Heidelberg, 2001).
6. Danishefsky, J.S. & Allen, J.R. Fromthe laboratory to the clinic: A retrospective on fully synthetic carbohydrate-based anticancer vaccines. Angew. Chem. Int. Ed. Engl. 39, 836-863 (2000).
7. Schips, C. & Ziegler, T. A practical one-pot synthesis of new S-glycosyl amino acid building blocks for combinatorial neoglycopeptide synthesis. J. Carbohydr. Chem. 24, 773-788 (2005).
8. Frank, R. Spot-synthesis: An easy technique for the positionally addressable, parallel chemical synthesis on a membrane support. Tetrahedron 48, 9217-9232 (1992).
9. Frank, R. The SPOT-synthesis technique. Synthetic peptide arrays on membrane supports∥inciples and applications. J. Immunol. Methods 267, 13-26 (2002).
10. Toepert, F. et al. Combining SPOT synthesis and native peptide ligation to create large arrays of WW protein domains. Angew. Chem. Int. Ed. Engl. 42, 1136-1140 (2003).
11. Rink, H. Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenyl-methyl ester resin. Tetrahedron Lett. 28, 3787-3790 (1987).