Chemical Tools to Study Bacterial Glycans: A Tale from Discovery of Glycoproteins to Disruption of Their Function

Barrett, Katharine; Dube, Danielle H.

doi:10.1002/ijch.202200050

Cited by 5 publications

(4 citation statements)

References 118 publications

(161 reference statements)

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“…Bacteria coat themselves with a dense array of cell envelope glycans that enhance bacterial fitness and promote survival. 40 Within a microbial aggregate, this sweet coat may end up as a component of the EPS. Additionally, glycans are specifically produced within the extracellular space.…”

Section: ■ Discussionmentioning

confidence: 99%

“…In comparison, mammalian cells construct their cell surface glycans using only nine monosaccharide building blocks, plants use 12 monosaccharides, whereas >700 monosaccharides have been found in bacterial glycans. 40 Moreover, unlike DNA replication or protein translation, glycan biosynthesis is not directed by a preexisting template molecule. Instead, the production of glycans is decided by a few factors: the biosynthetic machinery, the available nucleotide sugars (which serve as monosaccharide donors), and signals from the intracellular and extracellular environment.…”

Section: ■ Discussionmentioning

confidence: 99%

“…The study of bacterial glycans is further complicated by their enormous structural diversity. In comparison, mammalian cells construct their cell surface glycans using only nine monosaccharide building blocks, plants use 12 monosaccharides, whereas >700 monosaccharides have been found in bacterial glycans …”

Section: Discussionmentioning

confidence: 99%

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Sweet Secrets: Exploring Novel Glycans and Glycoconjugates in the Extracellular Polymeric Substances of “Candidatus Accumulibacter”

Páez-Watson,

Tomás-Martínez,

de Wit

et al. 2024

ACS EST Water

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Biological wastewater treatment relies on microorganisms that grow as flocs, biofilms, or granules for efficient separation of biomass from cleaned water. This biofilm structure emerges from the interactions between microbes that produce, and are embedded in, extracellular polymeric substances (EPS). The true composition and structure of the EPS responsible for dense biofilm formation are still obscure. We conducted a bottom-up approach utilizing advanced glycomic techniques to explore the glycan diversity in the EPS from a highly enriched "Candidatus Accumulibacter" granular sludge. Rare novel sugar monomers such as N-Acetylquinovosamine (QuiNAc) and 2-O-Methylrhamnose (2-OMe-Rha) were identified to be present in the EPS of both enrichments. Further, a high diversity in the glycoprotein structures of said EPS was identified by means of lectin based microarrays. We explored the genetic potential of "Ca. Accumulibacter" high quality metagenome assembled genomes (MAGs) to showcase the shortcoming of top-down bioinformatics based approaches at predicting EPS composition and structure, especially when dealing with glycans and glycoconjugates. This work suggests that more bottom-up research is necessary to understand the composition and complex structure of EPS in biofilms since genome based inference cannot directly predict glycan structures and glycoconjugate diversity.

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Section: ■ Discussionmentioning

confidence: 99%

Section: ■ Discussionmentioning

confidence: 99%

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Sweet Secrets: Exploring Novel Glycans and Glycoconjugates in the Extracellular Polymeric Substances of “Candidatus Accumulibacter”

Páez-Watson,

Tomás-Martínez,

de Wit

et al. 2024

ACS EST Water

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“…Because glycan biosynthesis is not directly genetically encoded, installing labels through genetic manipulation is difficult . Metabolic incorporation offers an incisive route to installing handles into glycans. − The process involves multistep, intracellular processing of simple monosaccharide building blocks by endogenous metabolic machinery, culminating in the presentation of the end products on the cell surface . Though several successful examples have been demonstrated in bacteria, applying this strategy in these organisms poses challenges due to the complexity of glycan metabolism and catabolism in bacteria. ,,− …”

Section: Introductionmentioning

confidence: 99%

Selective Glycan Labeling of Mannose-Containing Glycolipids in Mycobacteria

Lee,

Marando,

Smelyansky

et al. 2023

J. Am. Chem. Soc.

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Mycobacterium tuberculosis (Mtb) is one of history's most successful human pathogens. By subverting typical immune responses, Mtb can persist within a host until conditions become favorable for growth and proliferation. Virulence factors that enable mycobacteria to modulate host immune systems include a suite of mannose-containing glycolipids: phosphatidylinositol mannosides, lipomannan, and lipoarabinomannan (LAM). Despite their importance, tools for their covalent capture, modification, and imaging are limited. Here, we describe a chemical biology strategy to detect and visualize these glycans. Our approach, biosynthetic incorporation, is to synthesize a lipid-glycan precursor that can be incorporated at a latestage step in glycolipid biosynthesis. We previously demonstrated selective mycobacterial arabinan modification by biosynthetic incorporation using an exogenous donor. This report reveals that biosynthetic labeling is general and selective: it allows for cell surface mannose-containing glycolipid modification without nonspecific labeling of mannosylated glycoproteins. Specifically, we employed azido-(Z,Z)-farnesyl phosphoryl-β-D-mannose probes and took advantage of the strain-promoted azide−alkyne cycloaddition to label and directly visualize the localization and dynamics of mycobacterial mannose-containing glycolipids. Our studies highlight the generality and utility of biosynthetic incorporation as the probe structure directs the selective labeling of distinct glycans. The disclosed agents allowed for direct tracking of the target immunomodulatory glycolipid dynamics in cellulo. We anticipate that these probes will facilitate investigating the diverse biological roles of these glycans.

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Recent Advances in Protein‐Specific Glycan Imaging and Editing

Zheng

Meng

et al. 2023

ChemBioChem

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Chemical Tools to Study Bacterial Glycans: A Tale from Discovery of Glycoproteins to Disruption of Their Function

Abstract: This review is dedicated to Professor Carolyn Bertozzi, who has inspired a whole generation of chemical biologists.

Cited by 5 publications

References 118 publications

Sweet Secrets: Exploring Novel Glycans and Glycoconjugates in the Extracellular Polymeric Substances of “Candidatus Accumulibacter”

Sweet Secrets: Exploring Novel Glycans and Glycoconjugates in the Extracellular Polymeric Substances of “Candidatus Accumulibacter”

Selective Glycan Labeling of Mannose-Containing Glycolipids in Mycobacteria

Recent Advances in Protein‐Specific Glycan Imaging and Editing

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