Metabolic labeling of fucosylated glycoproteins in Bacteroidales species

Christen Besanceney-Webler; Hao Jiang; Wei Wang; Anthony D. Baughn; Peng Wu

doi:10.1016/j.bmcl.2011.05.038

Metabolic labeling of fucosylated glycoproteins in Bacteroidales species

Christen Besanceney-Webler, Hao Jiang, Wei Wang, Anthony D. Baughn, Peng Wu

Microbiology

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

Abstract

Members of the Bacteroidales order are among the most abundant gram-negative bacteria of the human colonic microbiota. These species decorate their cell-surface glycoproteins with fucosylated glycans, which are believed to play important roles in host intestinal colonization. Currently, there is no method for the enrichment of these glycoproteins for their identification. Here, we describe a chemical approach directed toward labeling and detecting fucosylated glycoproteins from cultured Bacteroidales species, namely Bacteroides fragilis and Parabacteroides distasonis. We treated these bacteria with an alkyne-bearing fucose analog, which is metabolically integrated into the bacterial surface fucosylated glycoproteins. The alkyne-tagged glycoproteins can then react with azide-bearing biophysical probes via bioorthogonal click chemistry for detection or glycoproteomic analysis.

Original language	English (US)
Pages (from-to)	4989-4992
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2011.05.038
State	Published - Sep 1 2011

Bibliographical note

Funding Information:
This work was supported by the National Institutes of Health (GM080585 to P.W.) and startup funds from Albert Einstein College of Medicine (to P.W.). C.B. is supported by the NIH training grant T32 GM007491. We thank Professor Laura Comstock for providing B. fragilis Δ fkp and Δ gmd mutants, and Professor Michael Malamy for providing B. fragilis 638R and pADB242A.

Keywords

Click chemistry
Fucosylated glycans
Metabolic engineering

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10.1016/j.bmcl.2011.05.038

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title = "Metabolic labeling of fucosylated glycoproteins in Bacteroidales species",

abstract = "Members of the Bacteroidales order are among the most abundant gram-negative bacteria of the human colonic microbiota. These species decorate their cell-surface glycoproteins with fucosylated glycans, which are believed to play important roles in host intestinal colonization. Currently, there is no method for the enrichment of these glycoproteins for their identification. Here, we describe a chemical approach directed toward labeling and detecting fucosylated glycoproteins from cultured Bacteroidales species, namely Bacteroides fragilis and Parabacteroides distasonis. We treated these bacteria with an alkyne-bearing fucose analog, which is metabolically integrated into the bacterial surface fucosylated glycoproteins. The alkyne-tagged glycoproteins can then react with azide-bearing biophysical probes via bioorthogonal click chemistry for detection or glycoproteomic analysis.",

keywords = "Click chemistry, Fucosylated glycans, Metabolic engineering",

author = "Christen Besanceney-Webler and Hao Jiang and Wei Wang and Baughn, {Anthony D.} and Peng Wu",

note = "Funding Information: This work was supported by the National Institutes of Health (GM080585 to P.W.) and startup funds from Albert Einstein College of Medicine (to P.W.). C.B. is supported by the NIH training grant T32 GM007491. We thank Professor Laura Comstock for providing B. fragilis Δ fkp and Δ gmd mutants, and Professor Michael Malamy for providing B. fragilis 638R and pADB242A. ",

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AU - Baughn, Anthony D.

AU - Wu, Peng

N1 - Funding Information: This work was supported by the National Institutes of Health (GM080585 to P.W.) and startup funds from Albert Einstein College of Medicine (to P.W.). C.B. is supported by the NIH training grant T32 GM007491. We thank Professor Laura Comstock for providing B. fragilis Δ fkp and Δ gmd mutants, and Professor Michael Malamy for providing B. fragilis 638R and pADB242A.

PY - 2011/9/1

Y1 - 2011/9/1

N2 - Members of the Bacteroidales order are among the most abundant gram-negative bacteria of the human colonic microbiota. These species decorate their cell-surface glycoproteins with fucosylated glycans, which are believed to play important roles in host intestinal colonization. Currently, there is no method for the enrichment of these glycoproteins for their identification. Here, we describe a chemical approach directed toward labeling and detecting fucosylated glycoproteins from cultured Bacteroidales species, namely Bacteroides fragilis and Parabacteroides distasonis. We treated these bacteria with an alkyne-bearing fucose analog, which is metabolically integrated into the bacterial surface fucosylated glycoproteins. The alkyne-tagged glycoproteins can then react with azide-bearing biophysical probes via bioorthogonal click chemistry for detection or glycoproteomic analysis.

AB - Members of the Bacteroidales order are among the most abundant gram-negative bacteria of the human colonic microbiota. These species decorate their cell-surface glycoproteins with fucosylated glycans, which are believed to play important roles in host intestinal colonization. Currently, there is no method for the enrichment of these glycoproteins for their identification. Here, we describe a chemical approach directed toward labeling and detecting fucosylated glycoproteins from cultured Bacteroidales species, namely Bacteroides fragilis and Parabacteroides distasonis. We treated these bacteria with an alkyne-bearing fucose analog, which is metabolically integrated into the bacterial surface fucosylated glycoproteins. The alkyne-tagged glycoproteins can then react with azide-bearing biophysical probes via bioorthogonal click chemistry for detection or glycoproteomic analysis.

KW - Click chemistry

KW - Fucosylated glycans

KW - Metabolic engineering

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Metabolic labeling of fucosylated glycoproteins in Bacteroidales species

Abstract

Bibliographical note

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