O-Alkyne-Trehalose (O-AlkTMM)

Catalog#
Unit Size
Price (USD)
Availability
Qty
1473-5
5 mg
$149.00
In stock
1473-25
25 mg
$480.00
In stock
1473-100
100 mg
$1,095.00
In stock

    Metabolic labeling with unnatural sugar substrates is a powerful alternative for investigating glycoconjugates in living organisms. Trehalose glycolipids can be metabolically labeled with O-Alkyne-Trehalose (O-AlkTMM) analogues in live mycobacteria, enabling bioorthogonal ligation with azide-functionalized fluorescent probes. This strategy can be used for imaging glycolipid distribution, trafficking, and dynamics as well as metabolite profiling and discovery.

    Molecular weight
    464.46
    Chemical composition
    C20H32O12
    CAS
    n/a
    Solubility
    Water, DMSO, DMF
    Purity
    >97% (H NMR)
    Appearance
    White to grey amorphous solid
    Storage conditions
    -20°C.
    Shipping conditions
    Ambient temperature

    Metabolic labeling with unnatural sugar substrates is a powerful alternative for investigating glycoconjugates in living organisms. Trehalose glycolipids can be metabolically labeled with O-Alkyne-Trehalose (O-AlkTMM) analogues in live mycobacteria, enabling bioorthogonal ligation with azide-functionalized fluorescent probes. This strategy can be used for imaging glycolipid distribution, trafficking, and dynamics as well as metabolite profiling and discovery. In addition, the O-AlkTMM may be employed to assess the effects of various perturbations (e.g., environmental stress, antibiotic treatment, genetic manipulation) on trehalose glycolipids and their associated biosynthetic pathways. O-AlkTMM analogue is likely to be metabolized in most, if not all, mycobacterial species given the highly conserved nature of the involved biosynthetic machinery. Importantly, the absence of trehalose metabolism in mammals invites the application of this chemical tool to investigate the trehalome during mycobacterial infection in host cells and model organisms.

    In summary, O-Alkyne-Trehalose enables sensitive, selective, and simultaneous detection of AGM and trehalose glycolipids in situ, providing a platform to study the mycomembrane in its native setting. O-AlkTMM is of particular interest because it allows rapid detection of the arabinogalactan mycolylation in whole cells for the first time. The TMM-based reporter are mycobacteria-specific, connoting potential for detection of bacteria in complex settings, for example, in sputum samples or during infection.

    1. Foley, H.N., et al. (2016). Bioorthogonal Chemical Reporters for Selective In Situ Probing of Mycomembrane Components in Mycobacteria.Angew. Chem. Int. Ed., 55: 2053–7. [PubMed]
    2. Fiolek, T.J., et al. (2019). Engineering the Mycomembrane of Live Mycobacteria with an Expanded Set of Trehalose Monomycolate Analogues.Chembiochem., 20: 1282-91. [PubMed]
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