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Biocatal Biotransformation 2010 Jan-Feb;28(1):41-50

Chemoenzymatic synthesis of conjugatable oligosialic acids

Mosley SL, Rancy PC, Peterson DC, Vionnet J, Saksena R, Vann WF

Abstract

Bacterial polysaccharides are components of glycoconjugate vaccines against encapsulated bacterial pathogens. Because these vaccines are prepared by random coupling methods the structure of the immunogens is difficult to characterize. As a model for the development of well-defined glycoconjugates we have devised a chemoenzymatic method for preparation of conjugatable oligosialic acids. In this scheme, chemically synthesized azide or alkyne derivatives of lactosides are sialylated by bacterial sialyltransferases. An HPLC method to follow the progress of the enzymatic reaction was developed based on fluorogenic coupling partners of the Huisgen 1,3-cycloaddition reaction, since the azide and alkyne aglycons are not convenient chromaphores. We have used this chemoenzymatic scheme to synthesize oligosialic acids of Neisseria meningitidis group C polysaccharide with a conjugatable aglycon. The chemoenzymatically synthesized oligosialic acids were coupled to bovine serum albumin with the 1,3-cycloaddition reaction. The resulting glycoconjugate was reactive with N. meningitidis group C-specific monoclonal antibody, thus confirming this as a possible pathway to glycoconjugate antigens.


Category: Journal Article
DOI: 10.3109/10242420903388694
Includes FDA Authors from Scientific Area(s): Biologics
Entry Created: 2011-10-04 Entry Last Modified: 2019-10-27
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