Development of highly pure alpha-helical lipoglycopeptides as self-adjuvanting vaccines

Zhong, Wei, Skwarczynski, Mariusz, Simerska, Pavla, Good, Michael F. and Toth, Istvan (2009) Development of highly pure alpha-helical lipoglycopeptides as self-adjuvanting vaccines. Tetrahedron, 65 17: 3459-3464. doi:10.1016/j.tet.2009.02.060


Author Zhong, Wei
Skwarczynski, Mariusz
Simerska, Pavla
Good, Michael F.
Toth, Istvan
Title Development of highly pure alpha-helical lipoglycopeptides as self-adjuvanting vaccines
Formatted title
Development of highly pure α-helical lipoglycopeptides as self-adjuvanting vaccines
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2009-04-25
Year available 2009
Sub-type Article (original research)
DOI 10.1016/j.tet.2009.02.060
Open Access Status
Volume 65
Issue 17
Start page 3459
End page 3464
Total pages 6
Place of publication East Park, Kidlington, Oxford, U.K.
Publisher Pergamon
Language eng
Subject C1
920108 Immune System and Allergy
920109 Infectious Diseases
030499 Medicinal and Biomolecular Chemistry not elsewhere classified
111504 Pharmaceutical Sciences
Abstract The incorporation of lipid moieties into synthetic peptide vaccines has been demonstrated to self-adjuvant otherwise poorly immunogenic peptides, whereas carbohydrates have emerged to be advantageous carriers for assembling these peptides. With the advent of an efficient native chemical ligation method, which is compatible with both peptides and carbohydrates, we have developed highly pure self-adjuvanting tetravalent group A streptococcal vaccine candidates assembled on carbohydrate templates. The utility of chemoselective ligation has overcome difficulties in the synthesis and purification of branched high molecular weight peptides. Circular dichroism measurements provided the evidence of alpha-helix formation of the assembled peptide epitopes, which may have impact on their immunogenicity. (C) 2009 Elsevier Ltd. All rights reserved.
Formatted abstract
The incorporation of lipid moieties into synthetic peptide vaccines has been demonstrated to self-adjuvant otherwise poorly immunogenic peptides, whereas carbohydrates have emerged to be advantageous carriers for assembling these peptides. With the advent of an efficient native chemical ligation method, which is compatible with both peptides and carbohydrates, we have developed highly pure self-adjuvanting tetravalent group A streptococcal vaccine candidates assembled on carbohydrate templates. The utility of chemoselective ligation has overcome difficulties in the synthesis and purification of branched high molecular weight peptides. Circular dichroism measurements provided the evidence of α-helix formation of the assembled peptide epitopes, which may have impact on their immunogenicity.
Keyword Chemistry, Organic
Chemistry
CHEMISTRY, ORGANIC
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2010 Higher Education Research Data Collection
ERA 2012 Admin Only
School of Chemistry and Molecular Biosciences
 
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Created: Thu, 03 Sep 2009, 18:17:18 EST by Mr Andrew Martlew on behalf of School of Chemistry & Molecular Biosciences