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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 40期

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

页码：10616 / 10619

页数：4

共 23 条

[1]

[Anonymous], 2010, ANGEW CHEM INT ED, V49, P1540

[2]

[Anonymous], 2007, ANGEW CHEM INT ED, V46, P5226

[3]

[Anonymous], 2010, Angew. Chem, V122, P1584, DOI DOI 10.1002/ANGE.200903924

[4]

[Anonymous], 2011, ANGEW CHEM INT ED, V50, P9611

[5] COVALENT LIPOPROTEIN FROM OUTER MEMBRANE OF ESCHERICHIA-COLI [J].

BRAUN, V .

BIOCHIMICA ET BIOPHYSICA ACTA, 1975, 415 (03) :335-377

[6] Fully Synthetic Self-Adjuvanting Thioether-Conjugated GlycopeptideLipopeptide Antitumor Vaccines for the Induction of Complement-Dependent Cytotoxicity against Tumor Cells [J].

Cai, Hui ;

Sun, Zhan-Yi ;

Huang, Zhi-Hua ;

Shi, Lei ;

Zhao, Yu-Fen ;

Kunz, Horst ;

Li, Yan-Mei .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) :1962-1970

[7] Towards a Fully Synthetic MUC1-Based Anticancer Vaccine: Efficient Conjugation of Glycopeptides with Mono-, Di-, and Tetravalent Lipopeptides Using Click Chemistry [J].

Cai, Hui ;

Huang, Zhi-Hua ;

Shi, Lei ;

Zhao, Yu-Fen ;

Kunz, Horst ;

Li, Yan-Mei .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (23) :6396-6406

[8] Vaccine Adjuvants: Putting Innate Immunity to Work [J].

Coffman, Robert L. ;

Sher, Alan ;

Seder, Robert A. .

IMMUNITY, 2010, 33 (04) :492-503

[9] A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol-Ene Coupling [J].

Dondoni, Alessandro ;

Massi, Alessandro ;

Nanni, Paolo ;

Roda, Aldo .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (43) :11444-11449

[10]

Eriksson EMY, 2007, CURR PROTEIN PEPT SC, V8, P412

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