Investigation of Monovalent and Bivalent Enantioselective Molecular Recognition by Electrospray Ionization-Mass Spectrometry and Tandem Mass Spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 19, Issue 11, 2008, Pages 1629-1642

  Schug, Kevin A ^a   Joshi, Manishkumar D ^a   Fryčák, Petr ^a   Maier, Norbert M ^b   Lindner, Wolfgang ^b  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BINDING ENERGY; CHIRALITY; CHROMATOGRAPHIC ANALYSIS; COMPUTER OPERATING PROCEDURES; DISSOCIATION; ELECTRON TRANSITIONS; ELECTROSPRAY IONIZATION; ENANTIOMERS; ENANTIOSELECTIVITY; FLOW INTERACTIONS; IONIZATION; IONIZATION OF GASES; ISOMERS; MASS SPECTROMETERS; MASS SPECTROMETRY; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; SEPARATION; SPECTROMETERS; SPECTROMETRY; SPECTRUM ANALYSIS; SYSTEMATIC ERRORS; TITRATION; VOLUMETRIC ANALYSIS;

BINDING CONSTANTS; DISSOCIATION ENERGIES; DISSOCIATION THRESHOLDS; EFFECTIVE CONCENTRATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SEPARATIONS; IN LINES; INTERACTION SYSTEMS; ION TRAPS; MECHANISTIC DIFFERENCES; MULTIPLE INTERACTIONS; MULTIVALENT INTERACTIONS; RELATIVE RESPONSE FACTORS; SPECTROMETRIC METHODS; STATIONARY PHASE; TANDEM MASS SPECTROMETRIES;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ARTICLE; BINDING AFFINITY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; TANDEM MASS SPECTROMETRY;

MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 55149119155     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.07.010     Document Type: Article

References (69)

1. Mammen M., Choi S.-K., and Whitesides G.M. Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. Angew. Chem. Int. Ed. 37 (1998) 2754-2794
2. Mulder A., Huskens J., and Reinhoudt D.N. Multivalency in Supramolecular Chemistry and Nanofabrication. Org. Biomol. Chem. 2 (2004) 3409-3424
3. Huskens J., Mulder A., Auletta T., Nijhuis C.A., Ludden M.J.W., and Reinhoudt D.N. A Model for Describing the Thermodynamics of Multivalent Host-Guest Interactions at Interfaces. J. Am. Chem. Soc. 126 (2004) 6784-6797
4. Rao J., and Whitesides G.M. Tight Binding of a Dimeric Vancomycin Derivative with Dimeric L-Lys-D-Ala-D-Ala. J. Am. Chem. Soc. 119 (1997) 10286-10290
5. Rao J., Lahiri J., Isaacs L., Weis R.M., and Whitesides G.M. A Trivalent System from Vancomycin·D-Ala-D-Ala with Higher Affinity Than Avidin·Biotin. Science 280 (1998) 708-711
6. Rao J., Yan L., Xu B., and Whitesides G.M. Using Surface Plasmon Resonance to Study the Binding of Vancomycin and its Dimer to Self-Assembled Monolayers Presenting D-Ala-D-Ala. J. Am. Chem. Soc. 121 (1999) 2629-2630
7. Nieto M., and Perkins H.R. Physicochemical Properties of Vancomycin and Iodovancomycin and Their Complexes with Diacetyl-L-lysyl-D-alanyl-D-alanine. Biochem. J. 123 (1971) 773-787
8. Nieto M., and Perkins H.R. Modification of the Acyl-D-Alanyl-D-Alanine Terminus Affecting Complex-Formation with Vancomycin. Biochem. J. 123 (1971) 789-803
9. Breslow R., and Chang B. Cholesterol Recognition and Binding by Cyclodextrin Dimers. J. Am. Chem. Soc. 118 (1996) 8495-8496
10. Fulton D.A., Cantrill S.J., and Stoddart J.F. Probing Polyvalency in Artificial Systems Exhibiting Molecular Recognition. J. Org. Chem. 67 (2002) 7968-7981
11. Badjic J.D., Cantrill S.J., Grubbs R.H., Guidry E.N., Orenes R., and Stoddart J.F. The Exclusivity of Multivalency in Dynamic Covalent Processes. Angew. Chem. Int. Ed. 43 (2004) 3273-3278
12. Badjic J.D., Nelson A., Cantrill S.J., Turnbull W.B., and Stoddart J.F. Multivalency and Cooperativity in Supramolecular Chemistry. Acc. Chem. Res. 38 (2005) 723-732
13. Badjic J.D., Ronconi C.M., Stoddart J.F., Balzani V., Silvi S., and Credi A. Operating Molecular Elevators. J. Am. Chem. Soc. 128 (2006) 1489-1499
14. Ludden M.J.W., Reinhoudt D.N., and Huskens J. Molecular Printboards: Versatile Platforms for the Creation and Positioning of Supramolecular Assemblies and Materials. Chem. Soc. Rev. 35 (2006) 1122-1134
15. Varki A. Biological Roles of Oligosaccharides: All of the Theories are Correct. Glycobiology 3 (1993) 97-130
16. Van Vliet L.D., Ellis T., Foley P.J., Liu L., Pfeffer F.M., Russell R.A., Warrener R.N., Hollfelder F., and Waring M.J. Molecular Recognition of DNA by Rigid [n]-Polynorbornane-Derived Bifunctional Intercalators: Synthesis and Evaluation of Their Binding Properties. J. Med. Chem. 50 (2007) 2326-2340
17. Edayathumangalam R.S., Weyermann P., Gottesfeld J.M., Dervan P.B., and Luger K. Molecular Recognition of the Nucleosomal "Supergroove.". Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 6864-6869
18. Pickens J.C., Mitchell D.D., Liu J., Tan X., Zhang Z., Verlinde C.L.M.J., Hol W.G.J., and Fan E. Nonspanning Bivalent Ligands as Improved Surface Receptor Binding Inhibitors of the Cholera Toxin B Pentamer. Chem. Biol. 11 (2004) 1205-1215
19. Ferguson M.R., Fan X., Mukherjee M., Luo J., Khan R., Ferreon J.C., Hilser V.J., Shope R.E., and Fox R.O. Directed Discovery of Bivalent Peptide Ligands to an SH3 Domain. Prot. Sci. 13 (2004) 626-632
20. Loidl G., Groll M., Musiol H.-J., Huber R., and Moroder L. Bivalency as a Principle for Proteasome Inhibition. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 5418-5422
21. Maier N.M., Franco P., and Lindner W. Separation of Enantiomers: Needs, Challenges, Perspectives. J. Chromatogr. A 906 (2001) 3-33
22. Pirkle W.H., and Pochapsky T.C. Separation of the Stereoisomers of a Homologous Series of bis-Amides on Chiral Stationary Phases. Chromatographia 25 (1988) 652-654
23. Pirkle W.H., and Readnour R.S. Chromatographic Approach to the Measurement of the Interstrand Distance for Some Chiral Bonded Phases. Anal. Chem. 63 (1991) 16-20
24. Ling F.H., Lu V., Svec F., and Fréchet J.M.J. Effect of Multivalency on the Performance of Enantioselective Separation Media for Chiral HPLC Prepared by Linking Multiple Selectors to a Porous Polymer Support via Aliphatic Dendrons. J. Org. Chem. 67 (2002) 1993-2002
25. Schug K.A., Fryčák P., Maier N.M., and Lindner W. Measurement of Solution-Phase Chiral Molecular Recognition in the Gas Phase Using Electrospray Ionization-Mass Spectrometry. Anal. Chem. 77 (2005) 3661-3671
26. Fryčák P., and Schug K.A. On-Line Dynamic Titration: Determination of Dissociation Constants for Noncovalent Complexes Using Gaussian Concentration Profiles by Electrospray Ionization-Mass Spectrometry. Anal. Chem. 79 (2007) 5407-5413
27. Schug K.A. Solution-Phase Enantioselective Recognition and Discrimination by Electrospray Ionization-Mass Spectrometry: State-of-the-Art Methods and an Eye Towards Increased Throughput Measurements. Comb. Chem. High Throughput Screening 10 (2007) 301-316
28. Fryčák P., and Schug K.A. Dynamic Titration: Determination of Dissociation Constants for Noncovalent Complexes in Multiplexed Format Using HPLC-ESI-MS. Anal. Chem. 80 (2008) 1385-1393
29. Loo J.A. Studying Noncovalent Protein Complexes by Electrospray Ionization Mass Spectrometry. Mass Spectrom. Rev. 16 (1997) 1-23
30. Veenstra T.D. Electrospray Ionization Mass Spectrometry in the Study of Biomolecular Noncovalent Interactions. Biophys. Chem. 79 (1999) 63-79
31. Brodbelt J.S. Probing Molecular Recognition by Mass Spectrometry. Int. J. Mass Spectrom. 200 (2000) 57-69
32. Schalley C.A. Molecular Recognition and Supramolecular Chemistry in the Gas Phase. Mass Spectrom. Rev. 20 (2001) 253-309
33. Daniel J.M., Friess S.D., Rajagopalan S., Wendt S., and Zenobi R. Quantitative Determination of Noncovalent Binding Interactions Using Soft Ionization Mass Spectrometry. Int. J. Mass Spectrom. 216 (2002) 1-27
34. Nesatyy V.J. Mass Spectrometry Evaluation of the Solution and Gas-Phase Properties of Noncovalent Protein Complexes. Int. J. Mass Spectrom. 221 (2002) 147-161
35. Heck A.J.R., and van den Heuvel R.H.H. Investigation of Intact Protein Complexes by Mass Spectrometry. Mass Spectrom. Rev. 23 (2004) 368-389
36. Di Tullio A., Reale S., and De Angelis F. Molecular Recognition by Mass Spectrometry. J. Mass Spectrom. 40 (2005) 845-865
37. Loo J.A., Holsworth D.D., and Root-Bernstein R.S. Use of Electrospray Mass Spectrometry to Probe Antisense Peptide Interactions. Biol. Mass Spectrom. 23 (1994) 6-12
38. Wang K., and Gokel G.W. Correlation of Solution- and Gas-Phase Complexation Assessed by Electrospray Ionization Mass Spectrometry: Application to One-, Two-, and Three-Ring Macrocycles. J. Org. Chem. 61 (1996) 4693-4697
39. Kempen E.C., and Brodbelt J.S. A Method for Determination of Binding Constants by Electrospray Ionization Mass Spectrometry. Anal. Chem. 72 (2000) 5411-5416
40. Dotsikas Y., and Loukas Y.L. Efficient Determination and Evaluation of Model Cyclodextrin Complex Binding Constants by Electrospray Mass Spectrometry. J. Am. Soc. Mass Spectrom. 14 (2003) 1123-1129
41. Wortmann A., Rossi F., Lelais G., and Zenobi R. Determination of Zinc to β-Peptide Binding Constants with Electrospray Ionization Mass Spectrometry. J. Mass Spectrom. 40 (2005) 777-784
42. Siebert H.-C., Lu S.-Y., Frank M., Kramer J., Wechselberger R., Joosten J., Andre S., Rittenhouse-Olson K., Roy R., von der Lieth C.-W., Kapstein R., Vliegenhart J.F.G., Heck A.J.R., and Gabius H.-J. Analysis of Protein-Carbohydrate Interaction at the Lower Size Limit of the Protein Part (15-Mer Peptide) by NMR Spectroscopy, Electrospray Ionization Mass Spectrometry, and Molecular Modeling. Biochemistry 41 (2002) 9707-9717
43. Young D.-S., Hung H.-Y., and Liu L.K. An Easy and Rapid Method for Determination of Stability Constants by Electrospray Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom. 11 (1997) 769-773
44. Sinz A., Jin A.J., and Zschörnig O. Evaluation of the Metal Binding Properties of a Histidine-Rich Fusogenic Peptide by Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. J. Mass Spectrom. 38 (2003) 1150-1159
45. Lim H.-K., Hsieh Y.L., Ganem B., and Henion J. Recognition of Cell-Wall Peptide Ligands by Vancomycin Group Antibiotics: Studies Using Ion Spray Mass Spectrometry. J. Mass Spectrom. 30 (1995) 708-714
46. Jorgensen T.J.D., Roepstorff P., and Heck A.J.R. Direct Determination of Solution Binding Constants for Noncovalent Complexes Between Bacterial Cell Wall Analogues and Vancomycin Group Antibiotics by Electrospray Ionization Mass Spectrometry. Anal. Chem. 70 (1998) 4427-4432
47. Seymour J.L., Turecek F., Malkov A.V., and Kocovsky P. Chiral Recognition in Solution and the Gas Phase. Experimental and Theoretical Studies of Aromatic D- and L-Amino Acid-Cu(II)-Chiragen Complexes. J. Mass Spectrom. 39 (2004) 1044-1052
48. Arakawa R., Kobayashi M., and Ama T. Chiral Recognition in Association between Antimony Potassium Tartarate and Bis(L-Alaninate)Ethylenediamine Cobalt(III) Complexes Using Electrospray Ionization Mass Spectrometry. J. Am. Soc. Mass Spectrom. 11 (2000) 804-808
49. Sawada M., Shizuma M., Takai Y., Yamada H., Kaneda T., and Hanafusa T. Enantioselectivity in FAB Mass Spectrometry. J. Am. Chem. Soc. 114 (1992) 4405-4406
50. Sawada M. Chiral Recognition Detected by Fast Atom Bombardment Mass Spectrometry. Mass Spectrom. Rev. 16 (1997) 73-90
51. Liang Y., Bradshaw J.S., Izatt R.M., Pope R.M., and Dearden D.V. Analysis of Enantiomeric Excess Using Mass Spectrometry: Fast Atom Bombardment/Sector and Electrospray Ionization/Fourier Transform Mass Spectrometric Approaches. Int. J. Mass Spectrom. (1999) 977-988 185/186/187
52. Filippi A., Giardini A., Piccirillo S., and Speranza M. Gas-Phase Enantioselectivity. Int. J. Mass Spectrom. 198 (2000) 137-163
53. Dearden D.V., Liang Y., Nicoll J.B., and Kellersberger K.A. Study of Gas-Phase Molecular Recognition Using Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. J. Mass Spectrom. 36 (2001) 989-997
54. Grigorean G., Gronert S., and Lebrilla C.B. Enantioselective Gas-Phase Ion/Molecule Reactions in a Quadrupole Ion Trap. Int. J. Mass Spectrom. 219 (2002) 79-87
55. Grigorean G., Cong X., and Lebrilla C.B. Chiral Analysis of Peptides by Ion/Molecule Reactions. Int. J. Mass Spectrom. 234 (2004) 71-77
56. Tao W.A., and Cooks R.G. Chiral Analysis by MS. Anal. Chem. 75 (2003) 25A-31A
57. Speranza M. Enantioselectivity in Gas-Phase Ion-Molecule Reactions. Int. J. Mass Spectrom. 232 (2004) 277-317
58. Schug K.A., and Lindner W. Chiral Molecular Recognition for the Detection and Analysis of Enantiomers by Mass Spectrometric Methods. J. Sep. Sci. 28 (2005) 1932-1955
59. Kitova E.N., Kitov P.L., Bundle D.R., and Klassen J.S. The Observation of Multivalent Complexes of Shiga-like Toxin with Globotriaoside and the Determination of their Stoichiometry by Nanoelectrospray Fourier-Transform Ion Cyclotron Resonance Mass Spectrometry. Glycobiology 11 (2001) 605-611
60. Broeren M.A.C., van Dongen J.L.J., Pittelkow M., Christensen J.B., van Genderen M.H.P., and Meijer E.W. Multivalency in the Gas Phase: The Study of Dendritic Aggregates by Mass Spectrometry. Angew. Chem. Int. Ed. 43 (2004) 3557-3562
61. Lämmerhofer M., and Lindner W. Quinine and Quinidine Derivatives as Chiral Selectors. I. Brush Type Chiral Stationary Phases for High Performance Liquid Chromatography based on Cinchonan Carbamates and Their Application as Chiral Anion Exchangers. J. Chromatogr. A 741 (1996) 33-48
62. Maier N.M., Schefzick S., Lombardo G.M., Feliz M., Rissanen K., Lindner W., and Lipkowitz K.B. Elucidation of the Chiral Recognition Mechanism of Cinchona Alkaloid Carbamate-type Receptors for 3,5-Dinitrobenzoyl Amino Acids. J. Am. Chem. Soc. 124 (2002) 8611-8629
63. Maier N.M., Nicoletti L., Lämmerhofer M., and Lindner W. Enantioselective Anion Exchangers Based on Cinchona Alkaloid-Derived Carbamates: Influence of C8/C9 Stereochemistry on Chiral Recognition. Chirality 11 (1999) 522-528
64. Schug K.A., and Lindner W. Using Electrospray Ionization-Mass Spectrometry/Tandem Mass Spectrometry and Small Molecules to Study Guanidinium-Anion Interactions. Int. J. Mass Spectrom. 241 (2005) 11-23
65. Wan K.X., Gross M.L., and Shibue T. Gas-Phase Stability of Double-Stranded Oligodeoxynucleotides and Their Noncovalent Complexes with DNA-Binding Drugs as Revealed by Collision Activation in an Ion Trap. J. Am. Soc. Mass Spectrom. 11 (2000) 450-457
66. Colorado A., and Brodbelt J. An Empirical Approach to Estimation of Critical Energies by Using a Quadrupole Ion Trap. J. Am. Soc. Mass Spectrom. 7 (1996) 1116-1125
67. Lah J., Maier N.M., Lindner W., and Vesnaver G. Thermodynamics of Binding of (R)- and (S)-Dinitrobenzoyl Leucine to Cinchona Alkaloids and their tert-Butylcarbamate Derivatives in Methanol: Evaluation of Enantioselectivity by Spectroscopic (CD, UV) and Microcalorimetric (ITC) Titrations. J. Phys. Chem. B 105 (2001) 1670-1678
68. Czerwenka C., Zhang M.M., Kählig H., Maier N.M., Lipkowitz K.B., and Lindner W. Chiral Recognition of Peptide Enantiomers by Cinchona Alkaloid Chiral Selectors: Mechanistic Investigations by Liquid Chromatography, NMR Spectroscopy, and Molecular Modeling. J. Org. Chem. 68 (2003) 8315-8327
69. Hirose K. A Practical Guide to Determination of Binding Constants. J. Incl. Phenom. Macrocycl. Chem. 39 (2001) 193-209