A practical one-pot synthesis of new S-glycosyl amino acid building blocks for combinatorial neoglycopeptide synthesis

Journal of Carbohydrate Chemistry

Volumn 24, Issue 8-9, 2005, Pages 773-788

  Schips, Carsten ^a   Ziegler, Thomas ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Amino acids; Glycoconjugate; Mitsunobu reaction; Thio glycosides

Indexed keywords

EID: 30344474258     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300500326859     Document Type: Article

References (27)

1. (a) Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. Synthesis of Sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition. J. Am. Chem. Soc. 1996, 118, 6826-6840;
2. (b) Lampe, T.F.J.; Weitz-Schmidt, G.; Wong, C.-H. Parallel synthesis of Sialyl Lewis X mimetics on a solid phase: access to a library of fucopeptides. Angew. Chem., Int. Ed. Engl. 1998, 37, 1707-1711.
3. (a) St. Hilaire, P.M.; Lowary, T.L.; Meldal, M.; Bock, K.J. Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries. Am. Chem. Soc. 1998, 120, 13312-13320;
4. (b) Christensen, M.K.; Meldal, M.; Bock, K.; Cordes, H.; Mouritsen, S.; Elsner, H.J. Synthesis of glycosylated peptide templates containing 6′-O-phosphorylated mannose disaccharides and their binding to the cation-independent mannose 6-phosphate receptor. Chem. Soc., Perkin Trans. 1 1994, 1299-1310;
5. (c) St. Hilaire, P.M.; Meldal, M. Glycopeptide and oligosaccharide libraries. Angew. Chem., Int. Ed. 2000, 39, 1162-1179.
6. (a) Jobron, L.; Hummel, G. Solid-phase synthesis of new S-glycoamino acid building blocks. Org. Lett. 2000, 2, 2265-2267;
7. (b) Zhu, X.; Haag, T.; Schmidt, R.R. Synthesis of an S-linked glycopeptide analog derived from human Tamm-Horsfall glycoprotein. Org. Biomol. Chem. 2004, 2, 31-33;
8. (c) Zhu, X.; Schmidt, R.R. Synthesis of α-S-linked glycopeptides in water containing solution. Tetrahedron Lett. 2003, 44, 6063-6067;
9. (d) Cohen, S.B.; Halcomb, R.L. Application of serine- and threonine-derived cyclic sulfamidates for the preparation of S-linked glycosyl amino acids in solution- and solid-phase peptide synthesis 2002, 124, 2534-2543.
10. Kutterer, K.M.K.; Barkley, A.; Arya, P. Glycomimitics: A programmed approach toward neoglycopeptide libraries. J. Comb. Chem. 2000, 2, 120-126.
11. Cohen, S.B.; Halcomb, R.L. Synthesis and characterization of an anomeric sulfur analogue of CMP-sialic acid. J. Org. Chem. 2000, 65, 6145-6152.
12. Driguez, H. Thiooligosaccharides as tools for structural biology. Chem. Bio. Chem. 2001, 2, 311-318.
13. Bertozzi, C.R.; Marcaurelle, L.A. New directions in the synthesis of glycopeptide mimetics. Chem. Eur. J. 1999, 5, 1384-1390.
14. Ziegler, T.; Röseling, D.; Subramanian, L.R. Preparation of glycosyl amino acids as building blocks for combinatorial synthesis of neoglycoconjugates. Tetrahedron: Asymmetry 2002, 13, 911-914.
15. (a) Ast, T.; Heine, N.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. Efficient assembly of peptomers on continuous surfaces. Tetrahedron Lett. 1999, 40, 4317-4318;
16. (b) Toepert, F.; Knaute, T.; Guffler, S.; Pirés, J.R.; Matzdorf, T.; Oschkinat, H.; Schneider-Mergener, J. Combining SPOT synthesis and native peptide ligation to create large arrays of WW protein dominas. Angew. Chem., Int. Ed. 2003, 42, 1136-1140.
17. 3 peptide capable of folding into a 12/10-helical secondary structure. Chem. Bio. Chem. 2003, 4, 1345-1347.
18. (a) Falconer, R.A.; Jablonkai, I.; Toth, I. Efficient synthesis of thioglycosides via Mitsunobu condensation. Tetrahedron Lett. 1999, 40, 8663-8666;
19. (b) Tsunoda, T.; Yamamiya, Y.; Ito, S. 1,1′-(Azodicarbonyl) dipiperidine-tributylphosphine, a new reagent system for Mitsunobu reaction. Tetrahedron Lett. 1993, 34, 1639-1642;
20. (c) Falk, J.R.; Jai, J.-Y.; Cho, S.S.-D.; Yu, J. Alkylthioether synthesis via imidazole mediated Mitsunobu condensation. Tetrahedron Lett. 1999, 40, 2903-2906;
21. (d) Huges, D.L. Org. React. 1992, 42, 335-656.
22. e) Review: Hillhouse Jr., J.H.; Valentine, D.H. Alkyl phosphines as reagents and catalysts in organic synthesis. Synthesis 2003, 317-334.
23. (a) Horton, D.L.; Wolfrom, M.L.; Thiosugars, I. Synthesis of derivatives of 2-amino-2-deoxy-1-thio-D-glucose. J. Org. Chem. 1962, 27, 1794-1800;
24. (b) Matta, K.L.; Girotra, R.N.; Barlow, J.J. Synthesis of p-nitrobenzyl and p-nitrophenyl 1-thioglycopyranosides. Carbohydr. Res. 1975, 43, 101-109;
25. (c) Durette, P.L.; Shen, T.Y. Insulin-like, and insulin-antagonistic, carbohydrate derivatives. The synthesis of aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides. Carbohydr. Res. 1980, 81, 261-274.
26. Carpino, L.A.; Grace, Y.H. 9-Fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 1972, 37, 3404-3409.
27. Lacombe, J.M.; Rakotomanomana, N.; Pavia, A.A. Free-radical addition of 1-thio-sugars to alkenes a new general approach to the synthesis of 1-thioglycosides. Tetrahedron Lett 1988, 29, 4239-4296.