title: Differentiation of Rubidiated Methyl-d-Glycoside Stereoisomers by Infrared Multiple-Photon Dissociation Spectroscopy in the O-H and C-H Stretching Regions.
abstract: Four isomeric sugar methylglycosides (α- and β-d-gluco- and galactopyranosides) were evaluated as rubidium cation coordination adducts in the gas phase using variable-wavelength multiple-photon dissociation in the range from 2750 to 3750 cm(-1). The adducts dissociated following photon absorption to yield neutral sugars and the rubidium cation, resulting in infrared "action" spectra. Well-resolved hydroxyl stretching bands clearly differentiate stereoisomers that vary solely in their asymmetry at single carbons. Density functional theory calculations of the lowest-energy gas-phase complexes indicate that rubidium coordinates with lone pairs of oxygen atoms as either bi- or tridentate complexes and that more than one positional coordination isomer could adequately account for most of the O-H stretch frequencies observed for each methylglycoside.
authors.affiliation: Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.
authors.forename: Wright L
authors.initials: WL
authors.lastname: Pearson
authors.affiliation: Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.
authors.forename: Cesar
authors.initials: C
authors.lastname: Contreras
authors.affiliation: Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.
authors.forename: David
authors.initials: D
authors.lastname: Powell
authors.affiliation: Radboud University , Institute for Molecules and Materials, FELIX Laboratory, Toernooiveld 7c, 6525 ED Nijmegen, The Netherlands.
authors.forename: Giel
authors.initials: G
authors.lastname: Berden
authors.affiliation: Radboud University , Institute for Molecules and Materials, FELIX Laboratory, Toernooiveld 7c, 6525 ED Nijmegen, The Netherlands.|University of Amsterdam , Science Park 904, 1098XH Amsterdam, The Netherlands.
authors.forename: Jos
authors.initials: J
authors.lastname: Oomens
authors.affiliation: Department of Cell and Developmental Biology and Program in Structural Biology and Biochemistry, University of Colorado Health Sciences Center , Denver, Colorado 80045, United States.
authors.forename: Brad
authors.initials: B
authors.lastname: Bendiak
authors.affiliation: Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.
authors.forename: John R
authors.initials: JR
authors.lastname: Eyler
mesh_terms: D002244:Carbon / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D017785:Photons; D012413:Rubidium / Q000737:chemistry*; D013055:Spectrophotometry, Infrared / Q000379:methods*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D006027:Glycosides; D002244:Carbon; D006859:Hydrogen; D012413:Rubidium; D010100:Oxygen