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Journal Article

Probing the glycosidic linkage: UV and IR ion-dip spectroscopy of a lactoside

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Meijer,  Gerard
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Helden,  Gert von
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Citation

Jockusch, R. A., Kroemer, R. T., Talbot, F. O., Snoek, L. C., Carcabal, P., Simons, J. P., et al. (2004). Probing the glycosidic linkage: UV and IR ion-dip spectroscopy of a lactoside. Journal of the American Chemical Society, 126(18), 5709-5714. doi:10.1021/ja031679k.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0011-0CB9-3
Abstract
The (14) glycosidic linkage found in lactose is a prevalent structural motif in many carbohydrates and glycoconjugates. Using UV and IR ion-dip spectroscopies to probe benzyl lactoside isolated in the gas phase, we find that the disaccharide unit adopts only a single, rigid structure. Its fully resolved infrared ion-dip spectrum is in excellent agreement with that of the global minimum structure computed ab initio. This has glycosidic torsion angles of H (H1-C1-O-C4') 180 and H (C1-O-C4'-H4') 0 which correspond to a rotation of ~150 about the glycosidic bond compared to the accepted solution-phase conformation. We discuss the biological implications of this discovery and the generality of the strategies employed in making it.