Restricted accessResearch articleFirst published online 2006-4
Supramolecular Clusters between Carbohydrates and Concave Pyridines. Detection in the Gas Phase by Resonance-Enhanced Multi-Photon Ionization Refectron Time-of-Fight Mass Spectrometry
For the first time, the formation of supramolecular clusters between concave pyridines and different carbohydrates could be observed in the gas phase. The different clusters have been investigated by means of laser desorption into a supersonic beam followed by resonant multi-photon excitation yielding mass spectra with high intensity of the different clusters. These preliminary results open the way for investigating the hydrogen bonds in these compounds.
AtwoodJ.L.SteedJ. (Eds), Encyclopedia of Supramolecular Chemistry.Marcel Dekker, New York, USA and references cited therein (2004).
2.
SartoriusJ.SchneiderH.-J., “A General Scheme for the Prediction of Hydrogen Bond Associations with Nucleobases and Synthetic Host Guest Complexes Based on Empirical Increments”, Chem. Eur. J.2, 1446 (1996).
3.
JorgensenW.L.PranataJ., “Importance of secondary interactions in triply hydrogen bonded complexes: Guaninecytosine vs uracil-2,6-diaminopyridine”, J. Am. Chem. Soc.112, 2008 (1990). doi: 10.1021/ja00161a061
4.
BrammerS.LüningU.KühlC., “A New Quadruply Bound Heterodimer DDAD-AAADA and Investigations into the Association Process”Eur. J. Org. Chem.4054 and references cited therein (2002).
5.
MayerM.F.NakashimaS.ZimmermanS.C., “Synthesis of a Soluble Ureido-Naphthyridine Oligomer that Self-Associates via Eight Contiguous Hydrogen Bonds”, Org. Lett.7, 3005 and references cited therein (2005). doi: 10.1021/o1050987f
6.
FranckA., “Aminkatalysierte Addition von Alkoholen an disubstituierte Ketene: Mechanismus und Stereoselektivität”, Dissertation, Freiburg, Germany (1985).
7.
JähmeJ.RüchardtC., “Basekatalysierte asymmetrische Induktion der Reaktion von Methyl(phenyl)keten mit 1-Phenylethanol: Gewinnung von Hydratropasäure in hoher Enantiomerenreinheit”, Angew. Chem.93, 919 (1981) and Angew. Chem., Int. Ed. Engl.20, 885 and references cited therein (1981).
8.
LüningU.BaumstarkR.SchyjaW., “Concave Reagents, 9: Alcoholysis of Diphenylketene Catalyzed by Concave Pyridines and Open-Chain Analogs”, Liebigs Ann. Chem.999 (1991).
9.
LüningU.PetersenS.SchyjaW.HackerW.MarquardtT.WagnerKBolteM., “Concave Reagents, 26: Concave Pyridines for Selective Acylations of Polyols”, Eur. J. Org. Chem.1077 and referencess cited therein (1998).
10.
PetersenS.LüningU., “Concave Reagents, 28: Comparison of Bimacrocyclic, Monomacrocyclic and Non-macrocyclic Bis(amidomethyl)pyridines as Catalysts in the Base Catalyzed Addition of Alcohols to Ketenes”, Eur. J. Org. Chem.847 (1999).
11.
GrotemeyerJ.BoeslU.WalterK.SchlagE.W.J., “Biomolecules in the Gas phase. I. Multiphoton Ionization Mass Spectrometry of Native Chlorophylls”, J. Am. Chem. Soc.108, 4233 and references cited therein (1986). doi: 10.1021/ja00274a069
12.
KarasM.BachmannD.BahrV.HillenkampF., “Matrix-assisted ultraviolet laser desorption of non-volatile compounds”, Int. J. Mass Spectrom. Proc.78, 53 (1987). doi: 10.1016/0168-1176(87)87041-6
13.
GrotemeyerJ.SchlagE.W., “Multiphoton-Ionisations-Massenspektrometrie; eine neues Hilfsmittel in der Analytik”, Angew. Chem.100, 461 (1988); Angew. Chem., Int. Ed. Engl.27, 447 (1988). doi: 10.1002/anie.198804473
14.
DeyM.GrotemeyerJ., “Cluster Formation of Biomolecules in the Gas Phase”, Eur. Mass Spectrom.1, 95 and references cited therein (1995).
15.
BeavisR.C.LindnerJ.GrotemeyerJ.SchlagE.W., “Infrared Desorption of Neutral Molecules Embedded in Transparent Matrices”, Z. Naturforsch.43a, 1083 (1988).
16.
(a) NirE.JanzenC.ImhofP.KleinermannsK.de VriesM.S., “Pairing of the nucleobases guanine and cytosine in the gas phase studied by IR–UV double-resonance spectroscopy and ab initio calculations”, Phys. Chem. Chem. Phys.4, 732 (2002). doi: 10.1039/b107429f; (b) NirE.JanzenC.ImhofP.KleinermannsK.de VriesM.S., “Pairing of the nucleobase guanine studied by IR-UV double-resonance spectroscopy and ab initio calculations”, Phys. Chem. Chem. Phys.4, 740 (2002). doi: 10.1039/b110360c
17.
GunzerF.GrotemeyerJ., “Enhancing of the signal-to-noise ratio in MATI spectra”, Int. J. Mass Spectrom.228, 921 (2003). doi: 10.1016/S1387-3806(03)00195-7
