Literature DB >> 23939951

Direct peptide lipidation through thiol-ene coupling enables rapid synthesis and evaluation of self-adjuvanting vaccine candidates.

Tom H Wright1, Anna E S Brooks, Alicia J Didsbury, Julie D MacIntosh, Geoffrey M Williams, Paul W R Harris, P Rod Dunbar, Margaret A Brimble.   

Abstract

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.

Entities:  

Keywords:  adjuvants; immunology; peptides; thiol-ene reaction; vaccines

Mesh：

Substances：

Year:  2013        PMID： 23939951     DOI： 10.1002/anie.201305620

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

1.  Synthesis and biological evaluation of S-lipidated lipopeptides of a connexin 43 channel inhibitory peptide.

Authors:  Sung-Hyun Yang; Connor A Clemett; Margaret A Brimble; Simon J O'Carroll; Paul W R Harris
Journal:  RSC Med Chem       Date:  2020-07-10

2.  S-Protected Cysteine Sulfoxide-Enabled Tryptophan-Selective Modification with Application to Peptide Lipidation.

Authors:  Daishiro Kobayashi; Eisuke Kuraoka; Junya Hayashi; Takuma Yasuda; Yutaka Kohmura; Masaya Denda; Norio Harada; Nobuya Inagaki; Akira Otaka
Journal:  ACS Med Chem Lett       Date:  2022-06-14       Impact factor: 4.632

Review 3.  Chemical Methods for Encoding and Decoding of Posttranslational Modifications.

Authors:  Kelly N Chuh; Anna R Batt; Matthew R Pratt
Journal:  Cell Chem Biol       Date:  2016-01-21       Impact factor: 8.116

4.  Chemical synthesis of the ATAD2 bromodomain.

Authors:  Gardner S Creech; Chelsea Paresi; Yue-Ming Li; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2014-02-10       Impact factor: 11.205

5.  NKT cell-dependent glycolipid-peptide vaccines with potent anti-tumour activity.

Authors:  Regan J Anderson; Benjamin J Compton; Ching-Wen Tang; Astrid Authier-Hall; Colin M Hayman; Gene W Swinerd; Renata Kowalczyk; Paul Harris; Margaret A Brimble; David S Larsen; Olivier Gasser; Robert Weinkove; Ian F Hermans; Gavin F Painter
Journal:  Chem Sci       Date:  2015-06-25       Impact factor: 9.825

6.  Interleukin-13 peptide vaccine induces protective humoral immunity in murine asthma models.

Authors:  Fengbo Wu; Yan Huang; Peng Zhang; Chunting Wang; Yaomei Tian; Lian Lu; Gu He; Li Yang
Journal:  Oncotarget       Date:  2017-08-04

7.  Double conjugation strategy to incorporate lipid adjuvants into multiantigenic vaccines.

Authors:  Waleed M Hussein; Tzu-Yu Liu; Pirashanthini Maruthayanar; Saori Mukaida; Peter M Moyle; James W Wells; Istvan Toth; Mariusz Skwarczynski
Journal:  Chem Sci       Date:  2016-01-04       Impact factor: 9.825

8.  Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo.

Authors:  Julien Poupart; Xin Hou; Sylvain Chemtob; William D Lubell
Journal:  Molecules       Date:  2019-11-15       Impact factor: 4.411

9.  "CLipP"ing on lipids to generate antibacterial lipopeptides.

Authors:  Victor Yim; Iman Kavianinia; Melanie K Knottenbelt; Scott A Ferguson; Gregory M Cook; Simon Swift; Aparajita Chakraborty; Jane R Allison; Alan J Cameron; Paul W R Harris; Margaret A Brimble
Journal:  Chem Sci       Date:  2020-05-20       Impact factor: 9.825

10.  The photochemical thiol-ene reaction as a versatile method for the synthesis of glutathione S-conjugates targeting the bacterial potassium efflux system Kef.

Authors:  Jess Healy; Tim Rasmussen; Samantha Miller; Ian R Booth; Stuart J Conway
Journal:  Org Chem Front       Date:  2016-02-26       Impact factor: 5.281
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