Probing the glycosidic linkage: UV and IR ion-dip spectroscopy of a lactoside |
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Authors: | Jockusch Rebecca A Kroemer Romano T Talbot Francis O Snoek Lavina C Carçabal Pierre Simons John P Havenith Martina Bakker Joost M Compagnon Isabelle Meijer Gerard von Helden Gert |
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Affiliation: | Department of Chemistry, Physical and Theoretical Chemistry Laboratory, Oxford University, Oxford OX1 3QZ, United Kingdom. |
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Abstract: | The beta(1-->4) 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 phi(H) (H1-C1-O-C4') approximately 180 degrees and psi(H) (C1-O-C4'-H4') approximately 0 degrees which correspond to a rotation of approximately 150 degrees 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. |
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