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Distinguishing Galactoside Isomers with Mass Spectrometry and Gas-Phase Infrared Spectroscopy.
Ho, Jordan S; Gharbi, Amira; Schindler, Baptiste; Yeni, Oznur; Brédy, Richard; Legentil, Laurent; Ferrières, Vincent; Kiessling, Laura L; Compagnon, Isabelle.
Afiliação
  • Ho JS; Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue Cambridge, Massachusetts 02139, United States.
  • Gharbi A; Univ. Lyon, Université Claude Bernard Lyon 1, CNRS, Institut Lumière Matière, F-69622 Villeurbanne, France.
  • Schindler B; Univ. Lyon, Université Claude Bernard Lyon 1, CNRS, Institut Lumière Matière, F-69622 Villeurbanne, France.
  • Yeni O; Univ. Lyon, Université Claude Bernard Lyon 1, CNRS, Institut Lumière Matière, F-69622 Villeurbanne, France.
  • Brédy R; Univ. Lyon, Université Claude Bernard Lyon 1, CNRS, Institut Lumière Matière, F-69622 Villeurbanne, France.
  • Legentil L; Univ. Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226 - ISCR, F-35000 Rennes, France.
  • Ferrières V; Univ. Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226 - ISCR, F-35000 Rennes, France.
  • Kiessling LL; Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue Cambridge, Massachusetts 02139, United States.
  • Compagnon I; Univ. Lyon, Université Claude Bernard Lyon 1, CNRS, Institut Lumière Matière, F-69622 Villeurbanne, France.
J Am Chem Soc ; 143(28): 10509-10513, 2021 07 21.
Article em En | MEDLINE | ID: mdl-34236183
Sequencing glycans is demanding due to their structural diversity. Compared to mammalian glycans, bacterial glycans pose a steeper challenge because they are constructed from a larger pool of monosaccharide building blocks, including pyranose and furanose isomers. Though mammalian glycans incorporate only the pyranose form of galactose (Galp), many pathogens, including Mycobacterium tuberculosis and Klebsiella pneumoniae, contain galactofuranose (Galf) residues in their cell envelope. Thus, glycan sequencing would benefit from methods to distinguish between pyranose and furanose isomers of different anomeric configurations. We used infrared multiple photon dissociation (IRMPD) spectroscopy with mass spectrometry (MS-IR) to differentiate between pyranose- and furanose-linked galactose residues. These targets pose a challenge for MS-IR because the saccharides lack basic groups, and galactofuranose residues are highly flexible. We postulated cationic groups that could complex through hydrogen bonding would offer a solution. Here, we present the first MS-IR analysis of hexose ammonium adducts. We compared their IR fingerprints with those of lithium adducts. We determined the diagnostic MS-IR signatures of the α- and ß-anomers of galactose in furanose and pyranose forms. We also showed these signatures could be applied to disaccharides to assign galactose ring size. Our findings highlight the utility of MS-IR for analyzing the unique substructures that occur in bacterial glycans.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Galactosídeos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Galactosídeos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Estados Unidos