Intriguing differences in the gas-phase dissociation behavior of protonated and deprotonated gonyautoxin epimers

Journal of the American Society for Mass Spectrometry

Volumn 22, Issue 11, 2011, Pages 2011-2020

  Dörr, Felipe A ^a   Kovačevi, Borislav ^b   Maksi, Zvonimir B ^b   Pinto, Ernani ^a   Volmer, Dietrich A ^c  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b RUDER BO KOVI INSTITUTE   (Croatia)

^c SAARLAND UNIVERSITY   (Germany)

Author keywords

Collision induced dissociation; Electrospray ionization; Epimers; Functional density theory; Gonyautoxins; Paralytic shellfish poisons; Toxins

Indexed keywords

COMPUTATION THEORY; CONFORMATIONS; DISSOCIATION; ELECTROSPRAY IONIZATION; GASES; IONIZATION OF GASES; MASS SPECTROMETRY; NEGATIVE IONS; PROTONATION;

COLLISION INDUCED DISSOCIATION; EPIMERS; FUNCTIONAL DENSITY; GONYAUTOXINS; PARALYTIC SHELLFISH POISONS; TOXINS;

DENSITY FUNCTIONAL THEORY;

GONYAUTOXIN; GONYAUTOXIN 1; GONYAUTOXIN 4; GONYAUTOXIN II; GONYAUTOXIN III; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; CONFORMATION; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY; ELECTROSPRAY MASS SPECTROMETRY; MATHEMATICAL COMPUTING; MATHEMATICAL MODEL; MOLECULAR WEIGHT; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 80755168410     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-011-0223-8     Document Type: Article

References (16)

1. B Luckas 1992 Phycotoxins in Seafood-Toxicological and Chromatographic Aspects J. Chromatogr. 624 439 456 10.1016/0021-9673(92)85694-O 1:CAS:528:DyaK38XmsFSjtL8%3D (Pubitemid 23008625)
2. GMA Hallegraeff 1993 Review of Harmful Algal Blooms and Their Apparent Global Increase Phycologia 32 79 99 10.2216/i0031-8884-32-2-79.1
3. Van Egmond, H.P., Aune, T., Lassus, P., Speijers, G.J.A., Waldock, M.: Paralytic and Diarrhetic Shellfish Poisons. Occurrence in Europe, Toxicity, Analysis, and Regulation. J. Nat. Toxins 2, 41-83 (1993)
4. MA Quilliam 2003 The Role of Chromatography in the Hunt for Red Tide Toxins J. Chromatogr. A 1000 527 548 10.1016/S0021-9673(03)00586-7 1:CAS:528:DC%2BD3sXktFGgsLs%3D (Pubitemid 36638473)
5. P Thibault S Pleasance M Laycock 1991 Analysis of Paralytic Shellfish Poisons by Capillary Electrophoresis J. Chromatogr. 542 483 501 10.1016/S0021-9673(01)88783-5 1:CAS:528:DyaK3MXisVantLo%3D
6. MA Quilliam M Janecek JF Lawrence 1993 Characterization of the Oxidation Products of Paralytic Shellfish Poisoning Toxins by Liquid Chromatography-Mass Spectrometry Rapid Commun. Mass Spectrom. 7 482 487 10.1002/rcm.1290070616 1:CAS:528:DyaK3sXltFSqt7k%3D
7. J Dahlmann WR Budakoswski B Luckas 2003 Liquid Chromatography- Electrospray Ionization Mass Spectrometry Based Methods for the Simultaneous Determination of Algal and Cyanobacterial Toxins in Phytoplankton from Marine Waters and Lakes Followed by Tentative Structural Elucidation of Microcystins J. Chromatogr. A 994 45 57 10.1016/S0021-9673(03)00485-0 1:CAS:528: DC%2BD3sXjtlWlur8%3D (Pubitemid 36553091)
8. O Arakawa T Noguchi Y Shida Y Onoue 1994 Occurrence of Carbamoyl-N-Hydroxy Derivatives of Saxitoxin and Neosaxitoxin in a Xanthid Crab Zosimus aeneus Toxicon 32 175 183 10.1016/0041-0101(94)90106-6 1:CAS:528:DyaK2cXitFSnsLY%3D (Pubitemid 24049774)
9. S Pleasance P Thibault J Kelly 1992 Comparison of Liquid-Junction and Coaxial Interfaces for Capillary Electrophoresis-Mass Spectrometry with Application to Compounds of Concern to the Aquaculture Industry J. Chromatogr. 591 325 339 10.1016/0021-9673(92)80250-X 1:CAS:528:DyaK38Xht1Oit7k%3D
10. RC Johnson Y Zhou K Statler J Thomas F Cox S Hall JR Barr 2009 Quantification of Saxitoxin and Neosaxitoxin in Human Urine Utilizing Isotope Dilution Tandem Mass Spectrometry J. Anal. Toxicol. 33 8 14 1:CAS:528: DC%2BD1MXlvFantQ%3D%3D
11. L Sleno DA Volmer B Kovačevi ZB Maksi 2004 Gas-phase Dissociation Reactions of Protonated Saxitoxin and Neosaxitoxin J. Am. Soc. Mass Spectrom. 15 462 477 10.1016/j.jasms.2003.11.013 1:CAS:528:DC%2BD2cXisVGhurw%3D (Pubitemid 38407132)
12. L Sleno DA Volmer AG Marshall 2005 Assigning Product Ions from Complex MS/MS Spectra: The Importance of Mass Uncertainty and Resolving Power J. Am. Soc. Mass Spectrom. 16 183 198 10.1016/j.jasms.2004.10.001 1:CAS:528: DC%2BD2MXht1CqtL8%3D (Pubitemid 40203142)
13. C Dell'Aversano P Hess MA Quilliam 2005 Hydrophilic Interaction Liquid Chromatography-Mass Spectrometry for the Analysis of Paralytic Shellfish Poisoning (PSP) Toxins J. Chromatogr. A 1081 190 201 10.1016/j.chroma.2005.05. 056 (Pubitemid 40848402)
14. Koch, W, Holthausen, M.C.: A Chemist's Guide to Density Functional Theory. Wiley-VCH, Weinheim/New York (2000).
15. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A. Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A.: Gaussian 03, Revision E.01. Gaussian, Inc., Wallingford CT (2004)
16. AD Boese JML Martin 2004 Development of Density Functionals for Thermochemical Kinetics J. Chem. Phys. 121 3405 3416 10.1063/1.1774975 1:CAS:528:DC%2BD2cXms1Kjtb4%3D