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

被引:50
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
    Wojcik, Felix
    O'Brien, Alexander G.
    Goetze, Sebastian
    Seeberger, Peter H.
    Hartmann, Laura
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (09) : 3090 - 3098
  • [22] A Method for the Generation of Pam2Cys-Based Lipopeptide Mimics via CuAAC Click Chemistry
    Yeung, Ho
    Lee, Dong Jun
    Williams, Geoffrey M.
    Harris, Paul W. R.
    Dunbar, Rod P.
    Brimble, Margaret A.
    [J]. SYNLETT, 2012, (11) : 1617 - 1620
  • [23] A Modular Approach to Assembly of Totally Synthetic Self-adjuvanting Lipopeptide-based Vaccines Allows Conformational Epitope Building
    Zeng, Weiguang
    Horrocks, Kylie J.
    Robevska, Gorjana
    Wong, Chinn Yi
    Azzopardi, Kristy
    Tauschek, Marija
    Robins-Browne, Roy M.
    Jackson, David C.
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (15) : 12944 - 12951