Conjugation-Amenable tetrasaccharide of the side chain of the major glycoprotein of the Bacillus anthracis exosporium: A large-scale preparation

Synthesis

Volumn , Issue 4, 2009, Pages 545-550

  Hou, Shujie ^a   Kováč, Pavol ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

Amines; Carbohydrates; Conjugation; Glycosylations; Oligosaccharides

Indexed keywords

ANTHROSE; BACILLUS ANTHRACIS; CHEMICAL MANIPULATIONS; CONJUGATE VACCINES; CONJUGATION; DE PROTECTIONS; GLYCOSYL DONORS; GLYCOSYLATIONS; NEW STRATEGIES; ONE POTS; SIDE CHAINS; SUGAR RESIDUES; SYNTHETIC APPROACHES; TETRASACCHARIDE;

AMINATION; AMINES; BACTERIOLOGY; CARBOHYDRATES; OLIGOSACCHARIDES; POLYSACCHARIDES; SUGAR (SUCROSE);

SYNTHESIS (CHEMICAL);

AMINE; GLYCOPROTEIN; SUGAR; TETRASACCHARIDE; VACCINE;

ANTHRAX; ARTICLE; BACILLUS ANTHRACIS; CONJUGATION; DEPROTECTION REACTION;

EID: 63849179286     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083338     Document Type: Article

References (19)

1. Daubenspeck, J. M.; Zeng, H.; Chen, P.; Dong, S.; Steichen, C. T.; Krishna, N. R.; Pritchard, D. G.; Turnbough, C. L. J. Biol. Chem. 2004, 279, 30945.
2. Saksena, R.; Adamo, R.; Kováĉ, P. Bioorg. Med. Chem. 2007, 15, 4283.
3. Adamo, R.; Saksena, R.; Kováĉ, P. Helv. Chim. Acta 2006, 89, 1075.
4. Werz, D. B.; Seeberger, P. H. Angew. Chem. Int. Ed. 2005, 44, 6315.
5. Crich, D.; Vinogradova, O. J. Org. Chem. 2007, 72, 6513.
6. Guo, H.; O'Doherty, G. A. Angew. Chem. Int. Ed. 2007, 46, 5206.
7. Hou, S.-j.; Kováĉ, P. Eur. J. Org. Chem. 2008, 1947.
8. Saksena, R.; Adamo, R.; Kováĉ, P. Carbohydr. Res. 2005, 540, 1591.
9. Mehta, A. S.; Saile, E.; Zhong, W.; Buskas, T.; Carlson, R.; Kannenberg, E.; Reed, Y.; Quinn, C. P.; Boons, G.-J. Chem. Eur. J. 2006, 12, 9136.
10. McNaught, A. D. Carbohydr. Res. 1997, 297, 1.
11. Tamborrini, M.; Werz, D. B.; Frey, J.; Pluschke, G.; Seeberger, P. H. Angew. Chem. Int. Ed. 2006, 45, 6581.
12. Hou, S.-j.; Saksena, R.; Kovac, P. Carbohydr. Res. 2008, 343, 196.
13. Tietze, L. F.; Schröter, C.; Gabius, S.; Brinck, U.; Goerlach-Graw, A.; Gabius, H.-J. Bioconjugate Chem. 1991, 2, 148.
14. Bioconjugate Techniques; Hermanson, G. T., Ed.; Academic Press: New York, 1996.
15. Lipták, A.; Szabó, L.; Harangi, J. J. Carbohydr. Chem. 1988, 7, 687.
16. Yu, H.; Yu, B.; Wu, X.; Hui, Y.; Han, X. J. Chem. Soc., Perkin Trans. 1 2000, 1445.
17. Fügedi, P.; Nánási, P. J. Carbohydr. Nucleosides, Nucleotides 1981, 8, 547.
18. Zemplén, G.; Geres, A.; Hadacsy, J. Ber. Dtsch. Chem. Ges. 1936, 69, 1827.
19. Thompson, A.; Wolfrom, M. L. Methods Carbohydr. Chem. 1963, 2, 215.