Subscribe to RSS
DOI: 10.1055/s-0028-1083338
Conjugation-Amenable Tetrasaccharide of the Side Chain of the Major Glycoprotein of the Bacillus anthracis Exosporium: A Large-Scale Preparation
Publication History
Publication Date:
27 January 2009 (online)

Abstract
A new strategy towards the synthesis of the title tetrasaccharide is described. The novelty within the common (2+2) assembly lies in the use of a disaccharide glycosyl donor having the fully assembled anthrose as one of the constituent sugar residues. Also, the final deprotection and transformation of the spacer arm into an amine, to form a structure amenable to conjugation by different conjugation techniques, is a one-pot conversion. Compared to other synthetic approaches, the present synthesis involves fewer chemical manipulations with the assembled tetrasaccharide as well as fewer overall numbers of synthetic steps towards this important antigenic component of a potential conjugate vaccine for anthrax.
Key words
carbohydrates - oligosaccharides - glycosylations - conjugation - amines
- Supporting Information for this article is available online:
- Supporting Information
- 1
Daubenspeck JM.Zeng H.Chen P.Dong S.Steichen CT.Krishna NR.Pritchard DG.Turnbough CL. J. Biol. Chem. 2004, 279: 30945 - 2
Saksena R.Adamo R.Kováč P. Bioorg. Med. Chem. 2007, 15: 4283 - 3
Adamo R.Saksena R.Kováč P. Helv. Chim. Acta 2006, 89: 1075 - 4
Werz DB.Seeberger PH. Angew. Chem. Int. Ed. 2005, 44: 6315 - 5
Crich D.Vinogradova O. J. Org. Chem. 2007, 72: 6513 - 6
Guo H.O’Doherty GA. Angew. Chem. Int. Ed. 2007, 46: 5206 - 7
Hou S.-j.Kováč P. Eur. J. Org. Chem. 2008, 1947 - 8
Saksena R.Adamo R.Kováč P. Carbohydr. Res. 2005, 340: 1591 - 9
Mehta AS.Saile E.Zhong W.Buskas T.Carlson R.Kannenberg E.Reed Y.Quinn CP.Boons G.-J. Chem. Eur. J. 2006, 12: 9136 - 10
McNaught AD. Carbohydr. Res. 1997, 297: 1 - 11
Tamborrini M.Werz DB.Frey J.Pluschke G.Seeberger PH. Angew. Chem. Int. Ed. 2006, 45: 6581 - 12
Hou S.-j.Saksena R.Kováč P. Carbohydr. Res. 2008, 343: 196 - 13
Tietze LF.Schröter C.Gabius S.Brinck U.Goerlach-Graw A.Gabius H.-J. Bioconjugate Chem. 1991, 2: 148 - 14
Bioconjugate
Techniques
Hermanson GT. 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 ML. Methods Carbohydr. Chem. 1963, 2: 215