title: Probing the mycobacterial trehalome with bioorthogonal chemistry.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Benjamin M
authors.initials: BM
authors.lastname: Swarts
authors.forename: Cynthia M
authors.initials: CM
authors.lastname: Holsclaw
authors.forename: John C
authors.initials: JC
authors.lastname: Jewett
authors.forename: Marina
authors.initials: M
authors.lastname: Alber
authors.forename: Douglas M
authors.initials: DM
authors.lastname: Fox
authors.forename: M Sloan
authors.initials: MS
authors.lastname: Siegrist
authors.forename: Julie A
authors.initials: JA
authors.lastname: Leary
authors.forename: Rainer
authors.initials: R
authors.lastname: Kalscheuer
authors.forename: Carolyn R
authors.initials: CR
authors.lastname: Bertozzi
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D006017:Glycolipids / Q000378:metabolism; D009161:Mycobacterium / Q000378:metabolism*; D014199:Trehalose / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000480:Alkynes; D001386:Azides; D005456:Fluorescent Dyes; D006017:Glycolipids; D014199:Trehalose