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

    Author(s)
    Zhong, Wei
    Skwarczynski, Mariusz
    Fujita, Yoshio
    Simerska, Pavla
    F. Good, Michael
    Toth, Istvan
    Griffith University Author(s)
    Good, Michael F.
    Year published
    2009
    Metadata
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    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 ...
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    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 a-helix bundles. The developed technique extends the use of carbohydrate templates and lipopeptide conjugates for producing self-adjuvanting and topology-controlled vaccine candidates.
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    Journal Title
    Australian Journal of Chemistry
    Volume
    62
    Issue
    9
    DOI
    https://doi.org/10.1071/CH09065
    Subject
    Infectious Diseases
    Chemical Sciences
    Publication URI
    http://hdl.handle.net/10072/38169
    Collection
    • Journal articles

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