Solid-Phase Synthesis of a 1-Thio-β-D-GlcNAc Carbohydrate Mimetic Library

Journal of Carbohydrate Chemistry

Volumn 22, Issue 7-8, 2003, Pages 781-800

  Hummel, Gerd ^a,b   Jobron, Laurence ^a,b   Hindsgaul, Ole ^a,c  

^a UNIVERSITY OF ALBERTA   (Canada)

^b Jerini AG   (Germany)

^c CARLSBERG LABORATORY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING PROTEIN; CARBOHYDRATE DERIVATIVE; GLUCOPYRANOSIDE; KETONE DERIVATIVE; N ACETYLGLUCOSAMINE; PROTEIN INHIBITOR; SUGAR;

ACYLATION; ALKYLATION; AMINATION; ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; MICHAEL ADDITION; REDUCTION; SOLID;

EID: 0346847619     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120026475     Document Type: Article

References (15)

1. Varki, A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 1993, 3, 97-130.
2. McAuliffe, J.C.; Hindsgaul, O. Carbohydrates in medicine. In Molecular and Cellular Glycobiology; Fukuda, M., Hindsgaul, O., Eds.; Oxford Univ. Press, 2000; 249-285.
3. Haase, W.-C.; Seeberger, P.H. Recent progress in polymer-supported synthesis of oligosaccharides and carbohydrate libraries. Curr. Org. Chem. 2000, 4, 481-511.
4. Seeberger, P.H.; Haase, W.-C. Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries. Chem. Rev. 2000, 100, 4349-4393.
5. Sofia, M.J.; Silva, D.J. Recent developments in solid-and solution-phase methods for generating carbohydrate libraries. Curr. Opin. Drug Discov. Dev. 1999, 2, 365-376.
6. Takuya, K.; Kanie, O. Carbohydrate-related libraries. Trends Glycosci. Glycotechnol. 1999, 11, 267-276.
7. Schweizer, F.; Hindsgaul, O. Combinatorial synthesis of carbohydrates. Curr. Opin. Chem. Biol. 1999, 3, 291-298.
8. Sofia, M.J. The generation of carbohydrate-based combinatorial libraries for drug discovery. Med. Chem. Res. 1998, 8, 362-378.
9. Sofia, M.J. Carbohydrate-based combinatorial libraries. J. Mol. Diversity 1998, 3, 75-94.
10. Nilsson, U.J.; Fournier, E.J.-L.; Fryz, E.J.; Hindsgaul, O. Parallel solution synthesis of a "carbohybrid" library designed to inhibit galactose-binding proteins. Comb. Chem. High Throughput Screen. 1999, 2, 335-352.
11. Nilsson, U.J.; Fournier, E.J.-L.; Hindsgaul, O. Solid-phase extraction on C18 silica as a purification strategy in the solution synthesis of a 1-thio-β-D-galactopyranoside library. Bioorg. Med. Chem. 1998, 6, 1563-1575.
12. Horton, D. 1-Thio-D-glucose. Methods Carbohydr. Chem. 1963, 2, 433-437.
13. Bennett, S.; von Itzstein, M.; Kiefel, M. A simple method for the preparation of thioglycosides of N-acetylneuraminic acid. Carbohydr. Res. 1994, 259, 293.
14. Abdel-Magid, A.F.; Carson, K.G.; Harris, B.D.; Maryanoff, C.A.; Shah, R.D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849-3862.
15. Ley, S.V.; Mynett, D.M.; Koot, W.-J. Solid phase synthesis of bicyclo[2.2.2]octane derivatives via tandem Michael addition reactions and subsequent reductive amination. Synlett 1995, 1017-1020.