Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry

被引：148

作者：

Swarts, Benjamin M. ^{[1
]}

Holsclaw, Cynthia M. ^{[4
,5
]}

Jewett, John C. ^{[1
]}

Alber, Marina ^{[6
]}

Fox, Douglas M. ^{[1
]}

Siegrist, M. Sloan ^{[1
]}

Leary, Julie A. ^{[4
]}

Kalscheuer, Rainer ^{[6
]}

Bertozzi, Carolyn R. ^{[1
,2
,3
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Univ Calif Berkeley, Dept Mol & Cell Biol, Berkeley, CA 94720 USA

[3] Univ Calif Berkeley, Howard Hughes Med Inst, Berkeley, CA 94720 USA

[4] Univ Calif Davis, Dept Mol & Cellular Biol, Davis, CA 95616 USA

[5] Univ Calif Davis, Campus Mass Spectrometry Facil, Davis, CA 95616 USA

[6] Univ Dusseldorf, Inst Med Microbiol & Hosp Hyg, D-40225 Dusseldorf, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 39期

关键词：

CELL-WALL CORE; TERMINAL ALKYNES; TUBERCULOSIS; MEMBRANE; BIOSYNTHESIS; TRANSPORTER; SMEGMATIS; PATHWAY; GROWTH; GLUCAN;

D O I：

10.1021/ja3062419

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in mycobacteria with azide-modified trehalose (TreAz) analogues. Subsequent bioorthogonal ligation with alkyne-functionalized probes enabled detection and visualization of cell-surface glycolipids. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome.

引用

页码：16123 / 16126

页数：4

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