Metabolic labeling of fucosylated glycoproteins in Bacteroidales species

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

Research output: Contribution to journalArticle

25 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)4989-4992
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number17
DOIs
StatePublished - Sep 1 2011

Fingerprint

Labeling
Glycoproteins
Bearings (structural)
Alkynes
Membrane Glycoproteins
Click Chemistry
Bacteroides fragilis
Bacteria
Fucose
Azides
Microbiota
Gram-Negative Bacteria
Polysaccharides

Keywords

  • Click chemistry
  • Fucosylated glycans
  • Metabolic engineering

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Metabolic labeling of fucosylated glycoproteins in Bacteroidales species. / Besanceney-Webler, Christen; Jiang, Hao; Wang, Wei; Baughn, Anthony D.; Wu, Peng.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 17, 01.09.2011, p. 4989-4992.

Research output: Contribution to journalArticle

Besanceney-Webler, C, Jiang, H, Wang, W, Baughn, AD & Wu, P 2011, 'Metabolic labeling of fucosylated glycoproteins in Bacteroidales species', Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 17, pp. 4989-4992. https://doi.org/10.1016/j.bmcl.2011.05.038
Besanceney-Webler, Christen ; Jiang, Hao ; Wang, Wei ; Baughn, Anthony D. ; Wu, Peng. / Metabolic labeling of fucosylated glycoproteins in Bacteroidales species. In: Bioorganic and Medicinal Chemistry Letters. 2011 ; Vol. 21, No. 17. pp. 4989-4992.
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