Total Syntheses of Mycolactone A/B and its Analogues for the Exploration of the Biology of Buruli Ulcer

被引：8

作者：

Saint-Auret, Sarah ^{[1
]}

Chany, Anne-Caroline ^{[1
]}

Casarotto, Virginie ^{[1
]}

Tresse, Cedric ^{[1
]}

Parmentier, Lise ^{[1
]}

Abdelkafi, Hajer ^{[1
]}

Blanchard, Nicolas ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Lab Chim Mol UMR 7509, F-67000 Strasbourg, France

来源：

CHIMIA | 2017年 / 71卷 / 12期

关键词：

Buruli ulcer; Diverted Total Synthesis; Mycolactone; Total Synthesis; MYCOBACTERIUM-ULCERANS; CHEMISTRY; PATHOGENESIS; PALLADIUM; HALIDES; TOXIN;

D O I：

10.2533/chimia.2017.836

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Buruli ulcer, classified as a neglected tropical disease by the World Health Organization, is caused by a mycobacterium which secretes a macrolidic exotoxin called mycolactone A/B. In this article, several synthetic strategies for the preparation of this toxin are discussed, highlighting the importance of total synthesis for the exploration of biological mechanism underpinning relevant human diseases.

引用

页码：836 / 840

页数：5

共 31 条

[1] Design, synthesis, and cytotoxicity of stabilized mycolactone analogs [J].

Babu, Vaddela Sudheer ;

Zhou, Ya ;

Kishi, Yoshito .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (05) :1274-1277

[2]

Blanchard N., 2015, STRATEGIES TACTICS O, V11, P85

[3] Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations [J].

Brown, Christopher A. ;

Aggarwal, Varinder K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (40) :13900-13903

[4] Synthetic Variants of Mycolactone Bind and Activate Wiskott-Aldrich Syndrome Proteins [J].

Chany, Anne-Caroline ;

Veyron-Churlet, Romain ;

Tresse, Cedric ;

Mayau, Veronique ;

Casarotto, Virginie ;

Le Chevalier, Fabien ;

Guenin-Mace, Laure ;

Demangel, Caroline ;

Blanchard, Nicolas .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (17) :7382-7395

[5] History, biology and chemistry of Mycobacterium ulcerans infections (Buruli ulcer disease) [J].

Chany, Anne-Caroline ;

Tresse, Cedric ;

Casarotto, Virginie ;

Blanchard, Nicolas .

NATURAL PRODUCT REPORTS, 2013, 30 (12) :1527-1567

[6] A Diverted Total Synthesis of Mycolactone Analogues: An Insight into Buruli Ulcer Toxins [J].

Chany, Anne-Caroline ;

Casarotto, Virginie ;

Schmitt, Marjorie ;

Tarnus, Celine ;

Guenin-Mace, Laure ;

Demangel, Caroline ;

Mirguet, Olivier ;

Eustache, Jacques ;

Blanchard, Nicolas .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (51) :14413-14419

[7]

Clavier H., 2009, EUR J ORG CHEM, V4254, DOI DOI 10.1002/ANIE.201709844

[8]

Cossy J., 2010, METATHESIS NATURAL P

[9]

Feyen F., 2007, SYNLETT, V415

[10] Complete structure of the mycolactones [J].

Fidanze, S ;

Song, FB ;

Szlosek-Pinaud, M ;

Small, PLC ;

Kishi, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) :10117-10118

← 1 2 3 4 →