Anomeric memory of the glycosidic bond upon fragmentation and its consequences for carbohydrate sequencing

Baptiste Schindler, Loïc Barnes, Gina Renois, Christopher Gray, Stéphane Chambert, Sébastien Fort, Sabine Flitsch, Claire Loison, Abdul-Rahman Allouche and Isabelle Compagnon ()
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Baptiste Schindler: Université de Lyon
Loïc Barnes: Université de Lyon
Gina Renois: Université de Lyon
Christopher Gray: The University of Manchester
Stéphane Chambert: Université de Lyon
Sébastien Fort: Université de Grenoble Alpes, CERMAV
Sabine Flitsch: The University of Manchester
Claire Loison: Université de Lyon
Abdul-Rahman Allouche: Université de Lyon
Isabelle Compagnon: Université de Lyon

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: Abstract Deciphering the carbohydrate alphabet is problematic due to its unique complexity among biomolecules. Strikingly, routine sequencing technologies—which are available for proteins and DNA and have revolutionised biology—do not exist for carbohydrates. This lack of structural tools is identified as a crucial bottleneck, limiting the full development of glycosciences and their considerable potential impact for the society. In this context, establishing generic carbohydrate sequencing methods is both a major scientific challenge and a strategic priority. Here we show that a hybrid analytical approach integrating molecular spectroscopy with mass spectrometry provides an adequate metric to resolve carbohydrate isomerisms, i.e the monosaccharide content, anomeric configuration, regiochemistry and stereochemistry of the glycosidic linkage. On the basis of the spectroscopic discrimination of MS fragments, we report the unexpected demonstration of the anomeric memory of the glycosidic bond upon fragmentation. This remarkable property is applied to de novo sequencing of underivatized oligosaccharides.

Date: 2017
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DOI: 10.1038/s41467-017-01179-y

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