Direct Peptide Lipidation through Thiol-Ene Coupling Enables Rapid Synthesis and Evaluation of Self-Adjuvanting Vaccine Candidates

被引:51
作者
Wright, Tom H. [1 ]
Brooks, Anna E. S. [2 ,3 ]
Didsbury, Alicia J. [2 ,3 ]
Williams, Geoffrey M. [1 ]
Harris, Paul W. R. [1 ,2 ]
Dunbar, P. Rod [2 ,3 ]
Brimble, Margaret A. [1 ,2 ,3 ]
机构
[1] Univ Auckland, Sch Chem Sci, Auckland Cent 1142, New Zealand
[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Auckland Cent 1142, New Zealand
[3] Univ Auckland, Sch Biol Sci, Auckland Cent 1142, New Zealand
关键词
adjuvants; immunology; peptides; thiol-ene reaction; vaccines; INNATE IMMUNITY;
D O I
10.1002/anie.201305620
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A radical lipidation: Application of a novel thiol-ene lipidation enables the one-step synthesis of self-adjuvanting antigenic peptides as vaccine candidates. The resultant monoacyl lipopeptides are shown to activate monocytes in a robust manner. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10616 / 10619
页数:4
相关论文
共 23 条
[21]   Synthesis of Carbohydrate-Functionalised Sequence-Defined Oligo(amidoamine)s by Photochemical ThiolEne Coupling in a Continuous Flow Reactor [J].
Wojcik, Felix ;
O'Brien, Alexander G. ;
Goetze, Sebastian ;
Seeberger, Peter H. ;
Hartmann, Laura .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (09) :3090-3098
[22]   A Method for the Generation of Pam2Cys-Based Lipopeptide Mimics via CuAAC Click Chemistry [J].
Yeung, Ho ;
Lee, Dong Jun ;
Williams, Geoffrey M. ;
Harris, Paul W. R. ;
Dunbar, Rod P. ;
Brimble, Margaret A. .
SYNLETT, 2012, (11) :1617-1620
[23]   A Modular Approach to Assembly of Totally Synthetic Self-adjuvanting Lipopeptide-based Vaccines Allows Conformational Epitope Building [J].
Zeng, Weiguang ;
Horrocks, Kylie J. ;
Robevska, Gorjana ;
Wong, Chinn Yi ;
Azzopardi, Kristy ;
Tauschek, Marija ;
Robins-Browne, Roy M. ;
Jackson, David C. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (15) :12944-12951