Antimony(III)-D, L-Tartrates Exhibit Proton-Assisted Enantioselective Binding in Solution and in the Gas Phase

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 11, 2009, Pages 2100-2105

  Wijeratne, Aruna B ^a   Spencer, Sandra E ^a   Gracia, Jose ^a   Armstrong, Daniel W ^a   Schug, Kevin A ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CE APPLICATIONS; CHIRAL SELECTOR; ENANTIOMERIC DISCRIMINATION; ENANTIOSELECTIVE; ENANTIOSELECTIVE BINDING; GASPHASE; IN-DEPTH STUDY; ISOTOPOMERS; MASS-SPECTRAL ANALYSIS; PROTONATED; TANDEM MASS SPECTROMETRY;

AMINES; AMINO ACIDS; ANTIMONY; MASS SPECTROMETRY; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; ORGANIC ACIDS; PROTONS; SPECTRUM ANALYSIS; SPECTRUM ANALYZERS;

EXPERIMENTS;

AMINO ACID; ANTIMONY TARTRATE; LEUCINE;

ARTICLE; BINDING COMPETITION; CAPILLARY ELECTROPHORESIS; CHIRALITY; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; TANDEM MASS SPECTROMETRY;

AMINO ACIDS; ANTIMONY; GASES; KINETICS; LEUCINE; MOLECULAR STRUCTURE; PHARMACEUTICAL SOLUTIONS; PHASE TRANSITION; PROTEIN BINDING; PROTONS; SOLUTIONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; TARTRATES;

EID: 70349778804     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2009.07.011     Document Type: Article

References (30)

1. Pasteur, L. Compt. Rend. Paris 1848, 26, 535-538.
2. Williams I.D., Pedersen S.F., Sharpless K.B., and Lippard S.J. Crystal Structures of Two Titanium Tartrate Asymmetric Epoxidation Catalysts. J. Am. Chem. Soc. 106 (1984) 6340-6341
3. Tapscott E.R., Belford R.L., and Paul I.C. Stereochemistry of Tartrato(4-)-Bridged Binuclear Complexes. Coord. Chem. Rev. 4 (1969) 323-359
4. Sun P., Krishnan A., Yadav A., Singh S., MacDonnell F.M., and Armstrong D.W. Enantiomeric Separations of Ruthenium(II) Polypyridyl Complexes Using High-Performance Liquid Chromatography (HPLC) with Cyclodextrin Chiral Stationary Phases (CSPs). Inorg. Chem. 46 (2007) 10312-10320
5. Nakazawa H., and Yoneda H. Chromatographic Study of Optical Resolution. II. Separation of Optically Active Cobalt(III) Complexes Using Potassium Antimony d-Tartrate as Eluent. J. Chromatogr. 160 (1978) 89-99
6. Martin S.E., Connatser R.M., Kane-Maguire N.A.P., and Wheeler J.F. Capillary Electrophoresis with Laser-Induced Fluorescence Detection for Chiral Analysis and DNA Binding Studies of Ruthenium(II) Tris-Diimine Complexes. Anal. Chim. Acta 445 (2001) 21-27
7. Plimmer H.G., and Bateman H.R. Further Results of the Experimental Treatment of Trypanosomiasis; Being a Progress Report of a Committee of the Royal Society. Proc. Royal Soc. London B 80 (1908) 477-487
8. Tracy J.W., and Webster L.T. Chemotherapy of Parasitic Infections. In: Hardman J.G., Limbird L.E., Molinoff P.B., Ruddon R.W., and Gilman A.G. (Eds). Goodman and Gilman's the Pharmacological Basis of Therapeutics. 9th ed. (1996), McGraw-Hill Book Co, New York 987-1008 Section IV.
9. Duffin J., and René P. "Anti-moine; anti-biotique": The Public Fortunes of the Secret Properties of Antimony Potassium Tartrate (Tartar Emetic). J. Hist. Med. Allied Sci. 46 (1991) 440-456
10. Mansour T.E. Chemotherapy of Parasitic Worms: New Biochemical Strategies. Science 205 (1979) 462-469
11. Brodbelt J.S. Probing Molecular Recognition by Mass Spectrometry. Int. J. Mass Spectrom. 200 (2000) 57-69
12. Gingras A.-C., Gstaiger M., Raught B., and Aebersold R. Analysis of Protein Complexes Using Mass Spectrometry. Nature Rev. 8 (2007) 645-654
13. 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. Combinat. Chem. High Throughput Screen. 10 (2007) 301-316
14. Arakawa R., Kobayashi M., and Ama T. Chiral Recognition in Association Between Antimony Potassium Tartrate and bis(L-Alaninate)Ethylenediamine Cobalt(III) Complexes Using Electrospray Ionization Mass Spectrometry. J. Am. Soc. Mass Spectrom. 11 (2000) 804-808
15. Arakawa R., Kobayashi M., Fukuo T., and Shiraiwa T. Studies on the Association of 2-Thiazolidinecarboxylic Acid and Antimony Potassium Tartrate: Chiral Recognition and Prediction of Absolute Configuration by Electrospray Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom. 15 (2001) 685-689
16. Wijeratne A.B., and Schug K.A. Molecular Recognition Properties of Tartrates and Metal-Tartrates in Solution and Gas Phase. J. Sep. Sci. 32 (2009) 1537-1547
17. Tian Z., and Kass S.R. Does Electrospray Ionization Produce Gas-Phase or Liquid-Phase Structures?. J. Am. Chem. Soc. 130 (2008) 10842-10843
18. Tian Z., Wang X., Wang L., and Kass S.R. Are Carboxyl Groups the Most Acidic Sites in Amino Acids?. Gas-Phase Acidities, Photoelectron Spectra, and Computations on Tyrosine, p-Hydroxybenzoic Acid, and Their Conjugate Bases. J. Am. Chem. Soc. 131 (2009) 1174-1181
19. Tian Z., and Kass S.R. Gas-Phase Versus Liquid-Phase Structures by Electrospray Ionization MassS. Angew. Chem 48 (2009) 1321-1323
20. Wu Z., Gao W., Phelps M.A., Wu D., Miller D.D., and Dalton J.T. Favorable Effects of Weak Acids on Negative-Ion Electrospray Ionization Mass Spectrometry. Anal. Chem. 76 (2004) 839-847
21. Kita K., Shiomi K., and Omura S. Advances in Drug Discovery and Biochemical Studies. Trends Parasitol. 23 (2007) 223-229
22. Schug K.A., Maier N.M., and Lindner W. Deuterium Isotope Effects Observed During Competitive Binding Chiral Recognition Electrospray Ionization-Mass Spectrometry of Cinchona Alkaloid-Based Systems. J. Mass Spectrom. 41 (2006) 157-161
23. Wan K.X., Gross M.L., and Shibue T. Gas-Phase Stability of Double-Stranded Oligodeoxynucleotides and Their Noncovalent Vomplexes with DNA-Binding Drugs as Revealed by Collisional Activation in an Ion Trap. J. Am. Soc. Mass Spectrom. 11 (2000) 450-457
24. Colorado A., and Brodbelt J.S. An Empirical Approach to Estimation of Critical Energies by Using a Quadrupole Ion Trap. J. Am. Soc. Mass Spectrom. 7 (1996) 1116-1125
25. Schug K.A., Joshi M.D., Fryčák P., Maier N.M., and Lindner W. Investigation of Monovalent and Bivalent Enantioselective Molecular Recognition by Electrospray Ionization-Mass Spectrometry and Tandem Mass Spectrometry. J. Am. Soc. Mass Spectrom. 19 (2008) 1629-1642
26. 1H-NMR. Proceedings of the 57th ASMS Conference on Mass Spectrometry and Allied Topics (May, 2009) Philadelphia, PA.
27. Wang X., Lee J.-T., and Armstrong D.W. Separation of Enantiomers by Capillary Electrophoresis Using Pentosan Polysulfate. Electrophoresis 20 (1999) 162-170
28. Trapp O., Trapp G., Kong J., Hahn U., Vogtle F., and Schurig V. Probing the Stereointegrity of Troger's Base-a Dynamic Electrokinetic Chromatographic Study. Chem. Eur. J 8 (2002) 3629-3634
29. Bustos E., Garcia J.E., Bandala Y., Godinez L.A., and Juaristi E. Enantioselective Recognition of Alanine in Solution with Modified Gold Electrodes Using Chiral PAMAM Dendrimers G4.0. Talanta 78 (2009) 1352-1358
30. Camara E., Green M.K., Penn S.G., and Lebrilla C.B. Chiral Recognition is Observed in the Deprotonation Reaction of Cytochrome c by (2R)- and (2S)-2-Butylamine. J. Am. Chem. Soc. 118 (1996) 8751-8752