Abstract
We studied the optical properties of gas-phase polysaccharides (maltose, maltotetraose, and maltohexaose) ions by action spectroscopy using the coupling between a quadrupole ion trap and a vacuum ultraviolet (VUV) beamline at the SOLEIL synchrotron radiation facility (France) in the 7 to 18 eV range. The spectra provide unique benchmarks for evaluation of theoretical data on electronic transitions of model carbohydrates in the VUV range. The effects of the nature of the charge held by polysaccharide ions on the relaxation processes were also explored. Finally the effect of isomerization of polysaccharides (with melezitose and raffinose) on their photofragmentation with VUV photons is presented.
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Heinze, T. (ed.): Polysaccharides I: Structure, Characterization, and Use. In: Advances in Polymer Science, vol. 186; Springer: Heidelberg, 2005, pp. 1–254
Lapasin,R., Pricl, S.: Rheology of Industrial Polysaccharides: Theory and Applications; Springer: Dordrecht, 1995, pp. 1–620
Dumitriu, S. (ed.): Polysaccharides. Structural Diversity and Functional Versatility, 2nd ed.; Marcel Dekker: New York, 2004
Bubb, W.A.: NMR spectroscopy in the study of carbohydrates: Characterizing the structural complexity. Concepts Magn. Reson. Part A 19A, 1–19 (2003)
Ghosh, D., Golan, A., Takahashi, L.K., Krylov, A.I., Ahmed, M.: A VUV photoionization and ab initio determination of the ionization energy of a gas-phase sugar (deoxyribose). J. Phys. Chem. Lett. 3, 97–101 (2012)
Arndt, E.R., Stevens, E.S.: VUV CD of simple saccharides. J. Am. Chem. Soc. 115, 7849–7853 (1993)
Johnson Jr., W.C.: CD spectroscopy and the VUV region. Ann. Rev. Phys. Chem. 29, 93–114 (1978)
Matsuo, K., Namatame, H., Taniguchi, M., Gekko, K.: VUV CD analysis of glycosaminglycans by SR spectroscopy. Biosci. Biotechnol. Biochem. 73, 557–561 (2009)
Nelson, R.G., Johnson Jr., W.C.: Optical properties of sugars. I. J. Am. Chem. Soc. 94, 3343–3345 (1972)
Nielsen, S.B., Chakraborty, T., Hoffmann, S.V.: SRCD spectroscopy of ribose and desoxyribose sugars, adenosine, AMP and dAMP nucleotides. Chem., Phys., Chem 6, 2619–2624 (2005)
Gekko, K., Yonehara, R., Sakurada, Y., Matsuo, K.: Structure analyses of biomolecules using a SR CD spectrophotometer. J. Electron. Spectrosc. 144/147, 295–297 (2005)
Matsuo, K., Gekko, K.: Vacuum-ultraviolet circular dichroism study of saccharides by synchrotron radiation spectrophotometry. Carbohydr. Res. 339, 591–597 (2004)
Dickinson, H.R., Johnson Jr., W.C.: Optical spectroscopy of sugars. II. J. Am. Chem. Soc. 96, 5050–5054 (1974)
Simons, J.P., Jockusch, R.A., Carcabal, P., Hung, I., Kroemer, R.T., Macleod, N.A., Snoek, L.C.: Sugars in the gas phase. Spectroscopy, conformation, hydration, cooperativity and selectivity. Int. Rev. Phys. Chem. 24, 489–531 (2005)
Carcabal, P., Jockusch, R.A., Hunig, I., Snoek, L.C., Kroemer, R.T., Davis, B.G., Gamblin, D.P., Compagnon, I., Oomens, J., Simons, J.P.: Hydrogen bonding and cooperativity in isolated and hydrated sugars: Mannose, galactose, glucose, and lactose. J. Am. Chem. Soc. 127, 11414–11425 (2005)
Reilly, J.P.: Ultraviolet photofragmentation of biomolecular ions. Mass Spectrom. Rev. 28, 425–447 (2009)
Devakumar, A., Thompson, M.S., Reilly, J.P.: Fragmentation of oligosaccharide ions with 157 nm vacuum ultraviolet light. Rapid Commun. Mass Spectrom. 19, 2313–2320 (2005)
Devakumar, A., Mechref, Y., Kang, P., Novotny, M.V., Reilly, J.P.: Identification of isomeric N-glycan structures by mass spectrometry with 157 nm laser-induced photofragmentation. J. Am. Soc. Mass Spectrom. 19, 1027–1040 (2008)
Devakumar, A., Mechref, Y., Kang, P., Novotny, M.V., Reilly, J.P.: Laser-induced photofragmentation of neutral and acidic glycans inside an ion-trap mass spectrometer. Rapid Commun. Mass Spectrom. 21, 1452–1460 (2007)
Ko, B.J., Brodbelt, J.S.: 193 nm Ultraviolet Photodissociation of Deprotonated Sialylated Oligosaccharides. Anal. Chem. 83, 8192–8200 (2011)
Antoine, R., Dugourd, P.: Visible and ultraviolet spectroscopy of gas phase protein ions. Phys. Chem. Chem. Phys. 13, 16494–16509 (2011)
Racaud, A., Allouche, A.R., Antoine, R., Lemoine, J., Dugourd, P.: UV electronic excitations in acidic sugars. J. Mol. Struct. (THEOCHEM) 960, 51–56 (2010)
Racaud, A., Antoine, R., Dugourd, P., Lemoine, J.: Photoinduced dissociation of heparin-derived oligosaccharides controlled by charge location. J. Am. Soc. Mass Spectrom. 21, 2077–2084 (2010)
Racaud, A., Antoine, R., Joly, L., Mesplet, N., Dugourd, P., Lemoine, J.: Wavelength-tunable ultraviolet photodissociation (UVPD) of heparin-derived disaccharides in a linear ion trap. J. Am. Soc. Mass Spectrom. 20, 1645–1651 (2009)
Brunet, C., Antoine, R., Allouche, A.R., Dugourd, P., Canon, F., Giuliani, A., Nahon, L.: Gas phase photo-formation and vacuum UV photofragmentation spectroscopy of tryptophan and tyrosine radical-containing peptides. J. Phys. Chem. A 115, 8933–8939 (2011)
Brunet, C., Antoine, R., Dugourd, P., Canon, F., Giuliani, A., Nahon, L.: Formation and fragmentation of radical peptide anions: Insights from vacuum ultra violet spectroscopy. J. Am. Soc. Mass Spectrom. 23, 274–281 (2012)
Milosavljevic, A.R., Nicolas, C., Gil, J.F., Canon, F., Refregiers, M., Nahon, L., Giuliani, A.: VUV synchrotron radiation: A new activation technique for tandem mass spectrometry. J. Sync. Rad. 19, 174–178 (2012)
Milosavljevic, A.R., Nicolas, C., Lemaire, J., Dehon, C., Thissen, R., Bizau, J.M., Refregiers, M., Nahon, L., Giuliani, A.: Photoionization of a protein isolated in vacuo. Phys. Chem. Chem. Phys. 13, 15432–15436 (2011)
Nahon, L., de Oliveira, N., Garcia, G.A., Gil, J.F., Pilette, B., Marcouille, O., Lagarde, B., Polack, F.: DESIRS: A state-of-the-art VUV beamline featuring high resolution and variable polarization for spectroscopy and dichroism at SOLEIL. J. Synchrot. Radiat. 19, 50–520 (2012)
Mercier, B., Compin, M., Prevost, C., Bellec, G., Thissen, R., Dutuit, O., Nahon, L.: Experimental and theoretical study of a differentially pumped absorption gas cell used as a low energy-pass filter in the vacuum ultraviolet photon energy range. J. Vac. Sci. Technol. A Vac. Surf. Films 18, 2533–2541 (2000)
Milosavljevic, A.R., Nicolas, C., Gil, J.F., Canon, F., Refregiers, M., Nahon, L., Giuliani, A.: Fast in vacuo photon shutter for synchrotron radiation quadrupole ion trap tandem mass spectrometry. Nucl. Instrum. Methods Phys. Res. Sect. B Beam Interact. Mater. Atoms 279, 34–36 (2012)
Larraillet, V., Antoine, R., Dugourd, P., Lemoine, J.: Activated-electron photodetachment dissociation for the structural characterization of protein polyanions. Anal. Chem. 81, 8410–8416 (2009)
Talbot, F.O., Tabarin, T., Antoine, R., Broyer, M., Dugourd, P.: Photo-Dissociation spectroscopy of trapped protonated tryptophan. J. Chem. Phys. 122, 074310 (2005)
Joly, L., Antoine, R., Allouche, A.R., Broyer, M., Lemoine, J., Dugourd, P.: Ultraviolet spectroscopy of peptide and protein polyanions in vacuo: Signature of the ionization state of tyrosine. J. Am. Chem. Soc. 129, 8428–8429 (2007)
Korth, M., Pitonak, M., Rezac, J., Hobza, P.: A transferable H-bonding correction for semiempirical quantum-chemical methods. J. Chem. Theory Comput. 6, 344–352 (2009)
Stewart, J.J.P.: Optimization of parameters for semiempirical methods. V. Modification of NDDO approximations and application to 70 elements. J. Mol. Model. 13, 1173–1213 (2007)
Swope, W.C., Andersen, H.C., Berens, P.H., Wilson, K.R.: A computer simulation method for the calculation of equilibrium constants for the formation of physical clusters of molecules: Application to small water clusters. J. Chem. Phys. 76, 637–649 (1982)
Bussi, G., Parrinello, M.: Stochastic thermostats: Comparison of local and global schemes. Comput. Phys. Commun. 179, 26–29 (2008)
Becke, A.D.: Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38, 3098–3100 (1988)
Becke, A.D.: Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648–5652 (1993)
Lee, C., Yang, W., Parr, R.: Development of the Colle-Salvetti Correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785–789 (1988)
Dunning Jr., T.H.: Rates of convergence and error estimation formulas for the Rayleigh-Ritz variational method. J. Chem. Phys. 90, 1007–1023 (1989)
Kendall, R.A., Dunning Jr., T.H., Harrison, R.J.: Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions. J. Chem. Phys. 96, 6796–6806 (1992)
Chai, J.-D., Head-Gordon, M.: Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys. Chem. Chem. Phys. 10, 6615–6620 (2008)
Tawada, Y., Tsuneda, T., Yanagisawa, S., Yanai, T., Hirao, K.: A long-range-corrected time-dependent density functional theory. J. Chem. Phys. 120, 8425–8433 (2004)
Antoine, R., Joly, L., Tabarin, T., Broyer, M., Dugourd, P., Lemoine, J.: Photo-induced formation of radical anion peptides. Electron photodetachment dissociation experiments. Rapid Commun. Mass Spectrom. 21, 265–268 (2007)
Joly, L., Antoine, R., Broyer, M., Lemoine, J., Dugourd, P.: Electron photodetachment from gas phase peptide dianions. Relation with optical absorption properties. J. Phys. Chem. A 112, 898–903 (2008)
Martin, R.L.: Natural transition orbitals. J. Chem. Phys. 118, 4775–4777 (2003)
Robin, M.B.: Higher excited states of polyatomic molecules, vol. III. Academic Press, Orlando (1985)
Cederbaum, L.S., Zobeley, J., Tarantelli, F.: Giant intermolecular decay and fragmentation of clusters. Phys. Rev. Lett. 79, 4778–4781 (1997)
Simons, J.: Molecular anions. J. Phys. Chem. A 112, 6401–6511 (2008)
Matheis, K., Joly, L., Antoine, R., Lepine, F., Bordas, C., Ehrler, O.T., Allouche, A.-R., Kappes, M.M., Dugourd, P.: Photoelectron spectroscopy of gramicidin polyanions: Competition between delayed and direct emission. J. Am. Chem. Soc. 130, 15903–15906 (2008)
Harvey, D.J.: Collision-induced fragmentation of underivatized N-linked carbohydrates ionized by electrospray. J. Mass Spectrom. 35, 1178–1190 (2000)
Lemoine, J., Fournet, B., Despeyroux, D., Jennings, K.R., Rosenberg, R., Dehoffmann, E.: Collision-induced dissociation of alkali-metal cationized and permethylated oligosaccharides—influence of the collision energy and of the collision gas for the assignment of linkage position. J. Am. Soc. Mass Spectrom. 4, 197–203 (1993)
Zucker, S., Lee, S., Webber, N., Valentine, S.J., Reilly, J.P., Clemmer, D.E.: An ion mobility/ion trap/photodissociation instrument for characterization of ion structure. J. Am. Soc. Mass Spectrom. 22, 1477–1485 (2011)
Lee, S., Valentine, S.J., Reilly, J.P., Clemmer, D.E.: Analyzing a mixture of disaccharides by IMS-VUVPD-MS. Int. J. Mass Spectrom. 309, 161–167 (2012)
Acknowledgments
The authors thank the Pôle Scientifique de Modélisation Numérique (PSMN) at Lyon, France, for generous computational facilities. SOLEIL support is acknowledged under project #20110002. This work was supported by the Agence Nationale de la Recherche Scientifique, France, under the project ANR-08-BLAN-0065. The authors also thank the general technical staff of SOLEIL for running the facility. They thank J.-F. Gil for his help in the alignment of the ion trap with respect to the beamline. They thank Stéphane Chambert, Sébastien Redon, and Francis Canon for helpful discussion.
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Enjalbert, Q., Brunet, C., Vernier, A. et al. Vacuum Ultraviolet Action Spectroscopy of Polysaccharides. J. Am. Soc. Mass Spectrom. 24, 1271–1279 (2013). https://doi.org/10.1007/s13361-013-0657-2
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DOI: https://doi.org/10.1007/s13361-013-0657-2