Metabolic labeling of glycans with unnatural sialic acid analogues has emerged as an invaluable tool for studying sialic acid biology. It has been showed that 9-azido-9-deoxy-N-acetylneuraminic acid (9AzNeu5Ac), a Neu5Ac analogue with the substitution of 9-hydroxyl group with an azide, could be metabolized and incorporated into sialoglycans in living cells and mice. The incorporated sialic acid analogue, 9AzNeu5Ac, enable visualization the cell-surface sialoglycans and glycoproteomic profiling by click-labeling with fluorophores and affinity tags, respectively.

Specifications

The post 9AzNue5Ac appeared first on VectorLabs.

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.

Specifications

The post O-Alkyne-Trehalose (O-AlkTMM) appeared first on VectorLabs.

Metabolic labeling with unnatural sugar substrates is a powerful alternative for investigating glycoconjugates in living organisms. Trehalose glycolipids can be metabolically labeled with 6-azide-modified trehalose (TreAz) analogues in live mycobacteria, enabling bioorthogonal ligation with alkyne-functionalized fluorescent probes. This strategy can be used for imaging glycolipid distribution, trafficking, and dynamics as well as metabolite profiling and discovery.

Specifications

The post 6-Azide-Trehalose (6-TreAz) appeared first on VectorLabs.

Ac4GalNAl is an unnatural alkyne-containing monosaccharide building block. The alkyne moiety can be used for modification though chemoselective ligation chemistries including CuAAC or various Pd-catalyzed coupling reactions. The acetyl groups increase solubility in many solvents and make handling of this building easier.

Specifications

The post N-(4-pentynoyl)-galactosamine tetraacylated (Ac4GalNAl) appeared first on VectorLabs.

Ac4GlcNAl is an unnatural alkyne-containing monosaccharide building block. The alkyne moiety can be used for modification though chemoselective ligation chemistries including CuAAC or various Pd-catalyzed coupling reactions. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.

Specifications

The post N-(4-pentynoyl)-glucosamine tetraacylated (Ac4GlcNAl) appeared first on VectorLabs.

Ac4ManNAl is an unnatural alkyne-containing monosaccharide building block. The alkyne moiety can be used for modification though chemoselective ligation chemistries including CuAAC or various Pd-catalyzed coupling reactions. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.

Specifications

The post N-(4-pentynoyl)-mannosamine-tetraacylated (Ac4ManNAl) appeared first on VectorLabs.

8-Azido-3,8-dideoxy-D-manno-octulosonic acid (Kdo Azide) is an analogue of the natural 3-deoxy-D-manno-octulosonic acid (Kdo) that contains a very small modification, specifically an azido moiety. This molecule can be incorporated by cultured cells (Gram-negative Bacteria, for example) and incorporated into glycans (LPS, for example) during active glycan biosynthesis. Detection utilizes the chemoselective ligation or “click” reaction between an azide and an alkyne or cyclooctyne.

Specifications

The post Kdo Azide appeared first on VectorLabs.

The unnatural azido-containing monosaccharide building block. The azide moiety can be used for modification though chemoselective ligation chemistries including CuAAC, Cu-free click reaction or Staudinger ligation. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.

Specifications

The post N-azidoacetylgalactosamine-tetraacylated (Ac4GalNAz) appeared first on VectorLabs.

The unnatural azido-containing monosaccharide building block. The azide moiety can be used for modification though chemoselective ligation chemistries including CuAAC, Cu-free click reaction or Staudinger ligation. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.

Specifications

The post N-azidoacetylglucosamine-tetraacylated (Ac4GlcNAz) appeared first on VectorLabs.

The unnatural azido-containing monosaccharide building block. The azide moiety can be used for modification though chemoselective ligation chemistries including CuAAC, Cu-free click reaction or Staudinger ligation. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.

Specifications

The post N-azidoacetylmannosamine-tetraacylated (Ac4ManNAz) appeared first on VectorLabs.