Gas-phase reactivity of silver and copper coordinated monosaccharide cations studied by electrospray ionization and tandem mass spectrometry

European Journal of Mass Spectrometry

Volumn 9, Issue 4, 2003, Pages 377-390

  Boutreau, Laurence ^c   Léon, Emmanuelle ^a   Salpin, Jean Yves ^a   Amekraz, Badia ^b   Moulin, Christophe ^b   Tortajada, Jeanine ^a  

^a Centre National de la Recherche Scientifique   (France)

^b CEA SACLAY   (France)

^c UCB PHARMA   (Belgium)

Author keywords

Cationization; Copper; DFT calculations; Electrospray; Gas phase; Glucosides; Mass spectrometry; Monosaccharides; Silver

Indexed keywords

2 METHYL ALPHA DEXTRO GLUCOSE; COORDINATION COMPOUND; COPPER; COPPER COMPLEX; FRUCTOSE; GALACTOSE; GLUCOSE; MONOSACCHARIDE; O METHYL BETA DEXTRO GLUCOSE; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; COMPLEX FORMATION; ISOMER; MASS SPECTROMETRY; STEREOISOMERISM; THEORY;

CATIONS; COPPER; FRUCTOSE; GALACTOSE; GASES; GLUCOSE; METHYLGLUCOSIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOSACCHARIDES; SILVER; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 0141608604     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.567     Document Type: Article

References (47)

1. D.M. Whitfield, S. Stojkovski and B. Sarkar, "Metal Coordination to Carbohydrates. Structures and Functions", Coordin. Chem. Rev. 122, 171-225 (1993).
2. S. Yano and M. Otsuka, Metal Ions in Biological Systems, Ed. by A. Sigel and H. Sigel. Marcel Dekker, New York, Vol. 32, p. 28 (1996).
3. Z. Zhou, S. Ogden and J.A. Leary, "Linkage Position Determination in Oligosaccharides: MS/MS Study of Lithium-Cationized Carbohydrates", J. Org. Chem. 55, 5444-5446 (1990).
4. A.R. Dongré and V.H. Wysocki, "Linkage Position of Lithium-Cationized Disaccharides by Surface-Induced Dissociation Tandem Mass Spectrometry", Org. Mass Spectrom. 29, 700-702 (1994).
5. E.M. Sible, S.P. Brimmer and J.A. Leary, "Interaction of First Row Transition Metals with α1-3,α1-6 Mannotriose and Conserved Trimannosyl Core Oligosaccharides: A Comparative Electrospray Ionization Study of Doubly and Singly Charged Complexes", J. Am. Soc. Mass Spectrom. 8, 32-42 (1997).
6. M.R. Asam and G.L. Glish, "Tandem Mass Spectrometry of Alkali Cationized Polysaccharides in a Quadrupole Ion Trap", J. Am. Soc. Mass Spectrom. 8, 987-995 (1997).
7. S. König and J.A. Leary, "Evidence for Linkage Position Determination in Cobalt Coordinated Pentasaccharides Using Ion Trap Mass Spectrometry", J. Am. Soc. Mass Spectrom. 9, 1125-1134 (1998).
8. J.M. Berjeaud, F. Couderc and J.C. Promé, "Stereochemically controlled decompostion of silver-cationized methyl glycosides", Org. Mass Spectrom. 28, 455-458 (1993).
9. 2+ cations with monosaccharides", Adv. Mass Spectrom. 15, 735-736 (2001).
10. 2+. Ions by Fast-Atom Bombardment and Tandem Mass Spectrometry" Eur. J. Mass Spectrom. 7, 321-330 (2001).
11. J-Y. Salpin and J. Tortajada, "Structural Characterization of Hexoses and Pentoses Using Lead Cationization. An Electrospray Ionization and Tandem Mass Spectrometric Study", J. Mass Spectrom. 37, 379-388 (2002).
12. (a) V. Carlesso, C. Afonso, F. Fournier and J-C. Tabet, "Stereochemical effects from doubly-charged iron clusters for the structural elucidation of diastereomeric monosaccharides using ESI/IT-MS", Int. J. Mass Spectrom. 219, 559-575 (2002);
13. +-Cationized Per-O-acetyland Per-O-benzyl-α-thioglycosides: a Collision-Induced Decomposition Study", Org. Mass Spectrom. 29, 238-246 (1994).
14. + Coordinated Mono- and Disaccharide Stereoisomers" Int. J. Mass Spectrom. 189, 189-204 (1999);
15. (b) E. Botek, J.L. Debrun, B. Hakim and L. Morin-Allory, "Attachment of alkali cations on β-D-glucopyranose: matrix-assisted laser desorption/ionization time of flight studies and ab initio calculations", Rapid Commun. Mass Spectrom. 15, 273-276 (2001);
16. + on glucose and on some of its methylated derivatives", Rapid Commun. Mass Spectrom. 17, 122-125 (2003).
17. S.P. Gaucher and J.A. Leary, "Stereochemical Differentiation of Mannose, Glucose, Galactose, and Talose Using Zinc(II) Diethylenetriamine and ESI-Ion Trap Mass Spectrometer", Anal. Chem. 70, 3009-3014 (1998).
18. H. Desaire and J.A. Leary, "Differentiation of Diastereoisomeric N-Acetylhexosamine Monosaccharides Using Ion Trap Tandem Mass Spectrometry", Anal. Chem. 71, 1997-2002 (1999).
19. (a) G. Smith, A. Kaffashan and J.A. Leary, "Influence of Coordination Number and Ligand Size On the Dissociation Mechanisms of Transition Metal-Monosaccharide Complexes", Int. J. Mass Spectrom. 182/183, 299-310 (1999);
20. (b) H. Desaire, M.D. Leavell and J. Leary, "Solvent Effects in Tandem Mass Spectrometry: Mechanistic Studies Indicating How a Change in Solvent Conditions and PH can Dramatically Alter CID spectra", J. Org. Chem. 67, 3693-3699 (2002).
21. (a) K.A. Jebber, K. Zhang, C.J. Cassady and A. Chung-Phillips, "Ab initio and Experimental studies of protonation of Glucose in the Gas Phase", J. Am. Chem. Soc. 118, 10515-10524 (1996);
22. (b) Y.J. Zeng, R.L. Ornstein and J.A. Leary, "A Density Functional Theory Investigation of Metal Ion Binding Sites in Monosacccharides", J. Mol. Struct. (Theochem) 389, 233-240 (1997);
23. (c) B. Ma, H.F. Schaeffer III and N.L. Allinger, "Theoretical studies of the potential Energy Surfaces and Compositions of Aldo- and Ketohexoses", J. Am. Chem. Soc. 120, 3411-3422 (1998);
24. (d) M. Hoffmann and J. Rychlewski, "Effects of Substituting a OH by a F Atom in D-Glucose. Ab Initio and DFT Analysis", J. Am. Chem. Soc. 123, 2308-2316 (2001).
25. 2+ with Mannose: a Density Functional Study", J. Mol. Struct. (Theochem) 536, 227-234 (2001).
26. + in the Gas Phase", J. Phys. Chem. A 106, 2641-2651 (2002).
27. J-Y. Salpin and J. Tortajada, "Gas-phase reactivity of Lead(II) ions with D-glucose. A combined electrospray ionization mass spectrometry and theoretical study", J. Phys. Chem. A 107, 2943-2953 (2003).
28. (a) J.J.P. Stewart, "Optimization of Parameters for Semiempirical Methods", J. Comput. Chem. 10, 209-220 (1989);
29. (b) A.D. Becke, "Density Functional Thermochemistry. 3. The Role of Exact Exchange", J. Chem. Phys. 98, 5648-5652 (1993);
30. (c) C. Lee, W. Yang and R.G. Parr, "Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density", Phys. Rev. B 37, 785-789 (1988).
31. + (M = Sc-Cu, La, Hf-Au)", J. Chem. Phys. 102, 4931-4941 (1995).
32. C. Adamo and F. Lelj, "A hybrid density functional study of the first-row transition-metal monocarbonyls", J. Chem. Phys. 103, 10605-10613 (1995).
33. M.R.A. Blomberg, P.E.M. Siegbahn and M. Svensson, "Comparisons of results from parametrized configuration interaction (PCI-80) and from hybrid density functional theory with experiments for first row transition metal compounds", J. Chem. Phys. 104, 9546-9554 (1996).
34. 2", J. Chem. Phys. 105, 9966-9971 (1996).
35. C.W. Bauschlicher, A. Ricca, H. Partridge and S.R. Langhoff, in Recent Advances in Density Functional Theory, Part II, Ed by D.P. Chong. World Scientific Publishing Company, Singapore (1997).
36. P.J. Hay and R.W. Wadt, "Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals", J. Chem. Phys. 82, 299-310 (1985).
37. + (M = Cu, Ag, and Au)", J. Phys. Chem. 100, 12253-12260 (1996);
38. +(S-2) complexes; The performance of different exchange and correlation functionals", J. Mol. Struct. (Theochem) 371, 313-324 (1996).
39. (a) Hyperchem release 6.01 for Windows. Hypercube, Inc. (1999);
40. (b) M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle and J.A. Pople, Gaussian 98, Revision A.7. Gaussian, Inc., Pittsburgh, PA (1998).
41. 2+ studied by electrospray ionization mass spectrometry" Int. J. Mass Spectrom. 185-187, 11-23 (1999);
42. (b) H. Lavanant, Y. Hoppilliard and H. Virelizier, "Reduction of copper(II) complexes by electron capture in an electrospray ionization source", J. Am. Soc. Mass Spectrom. 9, 1217-1121 (1998).
43. (a) C.L. Gatlin, F. Tureček and T. Vaisar, "Gas-Phase Complexes of Amino Acids With Cu(II) and Diimine Ligands 1. Aliphatic and aromatic Amino Acids", J. Mass Spectrom. 30, 1605-1616 (1995);
44. (b) C.L. Gatlin, F. Tureček and T. Vaisar, "Gas-Phase Complexes of Amino Acids With Cu(II) and Diimine Ligands 2. Amino Acids with O, N and S Functional Groups in the Side Chain", J. Mass Spectrom. 30, 1617-1627 (1995);
45. (c). T. Vaisar, C.L. Gatlin and F. Tureček, "Oxidation of Peptide-Copper Complexes by Alkali Metal Cations in the Gas Phase", J. Am. Chem. Soc. 118, 5314-5315 (1996);
46. (d) T. Vaisar, C.L. Gatlin, R.D. Rao, J.L. Seymour and F. Tureček, "Sequence information, distinction and quantitation of C-terminal leucine and isoleucine in ternary complexes of tripeptides with Cu(II) and 2,2′-bipyridine", J. Mass Spectrom. 36, 306-316 (2001).
47. + with Glycerol: an Experimental and Theoretical Study", J. Phys. Chem. A 106, 10563-10577 (2002).