Spectroscopic diagnostic for the ring-size of carbohydrates in the gas phase: furanose and pyranose forms of GalNAc

Baptiste Schindler; Laurent Legentil; Abdul-Rahman Allouche; Vincent Ferrières; Isabelle Compagnon

doi:10.1039/c8cp04082f

Spectroscopic diagnostic for the ring-size of carbohydrates in the gas phase: furanose and pyranose forms of GalNAc

Baptiste Schindler ¹ Laurent Legentil ² Abdul-Rahman Allouche ¹ Vincent Ferrières ^{2, *} Isabelle Compagnon ^{1, *}

* Corresponding author

1 ILM - Institut Lumière Matière [Villeurbanne]

2 ISCR - Institut des Sciences Chimiques de Rennes

Abstract : Hexoses are mainly found in nature in the pyranose form (6-membered ring). Yet, furanose forms (5-membered ring) are observed in some rare polysaccharides. Using IRMPD spectroscopy (InfraRed Multiple Photon Dissociation), we propose a straightforward diagnostic of the ring-size of N-acetyl galactosamine ions. The furanose form of N-acetyl galactosamine was synthesized and its protonated ion was isolated in an ion trap to measure its gas phase vibrational spectrum by IRMPD. Comparison with the IRMPD spectrum of its pyranose counterpart reveals that they have distinctive optical fingerprints. This new MS-based diagnostic opens the way to facile identification of the ring-size in oligosaccharides. Our experimental data also provide new insights to support the theoretical description of the conformational behavior of the furanose ring, which is notoriously more flexible than the pyranose form but remains difficult to assess.

Document type :

Journal articles

Domain :

Chemical Sciences / Analytical chemistry

Chemical Sciences / Theoretical and/or physical chemistry

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Spectroscopic diagnostic for the ring-size of carbohydrates in the gas phase: furanose and pyranose forms of GalNAc

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