Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

Fagan, Vincent, Toth, Istvan and Simerska, Pavla (2014) Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold. Beilstein Journal of Organic Chemistry, 10 1741-1748. doi:10.3762/bjoc.10.181


Author Fagan, Vincent
Toth, Istvan
Simerska, Pavla
Title Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold
Journal name Beilstein Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1860-5397
Publication date 2014-07-01
Sub-type Article (original research)
DOI 10.3762/bjoc.10.181
Open Access Status DOI
Volume 10
Start page 1741
End page 1748
Total pages 8
Editor V. Křen
Place of publication Frankfurt am Main, Germany
Publisher Beilstein - Institut zur Foerderung der Chemischen Wissenschaften
Language eng
Formatted abstract
A novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support. Four copies of a group A streptococcal B cell epitope (J8) were then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction. The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope.
Keyword Amino acid lipidation
Cycloadditon reaction
Multivalent glycosystems
Peptide vaccine
Tetrapropargyl glucopyranose
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
School of Pharmacy Publications
 
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Created: Sat, 30 Aug 2014, 00:19:20 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences