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          Institute: Fritz-Haber-Institut     Collection: Molecular Physics     Display Documents



ID: 122308.0, Fritz-Haber-Institut / Molecular Physics
Probing the glycosidic linkage: UV and IR ion-dip spectroscopy of a lactoside
Authors:Jockusch, Rebecca A; Kroemer, Romano T.; Talbot, Francis O.; Snoek, Lavina C.; Carcabal, Pierre; Simons, John P.; Havenith, Martina; Bakker, Joost M.; Compagnon, Isabelle; Meijer, Gerard; Helden, Gert von
Language:English
Date of Publication (YYYY-MM-DD):2004-04-09
Title of Journal:Journal of the American Chemical Society
Journal Abbrev.:J. Am. Chem. Soc.
Volume:126
Issue / Number:18
Start Page:5709
End Page:5714
Copyright:© 2004 American Chemical Society
Review Status:Peer-review
Audience:Experts Only
Abstract / Description: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.
External Publication Status:published
Document Type:Article
Communicated by:Gerard Meijer
Affiliations:Fritz-Haber-Institut/Molecular Physics
External Affiliations:Oxford University, UK; FOM Institute "Rijnhuizen", Nieuwegein, The Netherlands; Dept. Phys. Chem II, Ruhr Univ. Bochum, Germany.
Identifiers:URL:http://pubs.acs.org/cgi-bin/article.cgi/jacsat/200...
DOI:10.1021/ja031679k
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