Design and synthesis of lipopeptide-carbohydrate assembled multivalent vaccine candidates using native chemical ligation

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Title Design and synthesis of lipopeptide-carbohydrate assembled multivalent vaccine candidates using native chemical ligation
Author Zhong, Wei; Skwarczynski, Mariusz; Fujita, Yoshio; Simerska, Pavla; Good, Michael Francis; Toth, Istvan
Journal Name Australian Journal of Chemistry
Year Published 2009
Place of publication Australia
Publisher CSIRO Publishing
Abstract Development of a synthetic vaccine against group A streptococcal infection is increasingly paramount due to the induction of autoimmunity by the main virulent factor – M protein. Peptide vaccines, however, are generally poorly immunogenic, necessitating administration with carriers and adjuvants. One of the promising approaches to deliver antigenic peptides is to assemble peptides on a suitable template which directs the attached peptides to form a well defined tertiary structure. For self-adjuvanting human vaccines, the conjugation of immunostimulatory lipids has been demonstrated as a potentially safe method. This study describes the design and optimized synthesis of two lipopeptide conjugated carbohydrate templates and the assembling of peptide antigens. These lipopeptide–carbohydrate assembled multivalent vaccine candidates were obtained in high yield and purity when native chemical ligation was applied. Circular dichroism studies indicated that the template-assembled peptides form four α-helix bundles. The developed technique extends the use of carbohydrate templates and lipopeptide conjugates for producing self-adjuvanting and topology-controlled vaccine candidates.
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1071/CH09065
Volume 62
Issue Number 9
Page from 993
Page to 999
ISSN 0004-9425
Date Accessioned 2011-03-31
Language en_AU
Research Centre Institute for Glycomics
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Infectious Diseases
URI http://hdl.handle.net/10072/38169
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1x

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