Fragmentation of diketopiperazines from Aspergillus fumigatus by electrospray ionization tandem mass spectrometry (ESI-MS/MS)

Journal of Mass Spectrometry

Volumn 42, Issue 10, 2007, Pages 1279-1286

  Furtado, Niege A J C ^a,b   Vessecchi, Ricardo ^b   Tomaz, José Carlos ^b   Galembeck, Sérgio E ^b   Bastos, Jairo K ^b   Lopes, Norberto P ^b   Crotti, Antonio E M ^a  

^a UNIVERSIDADE DE FRANCA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Aspergillus fumigatus; Diketopiperazines; Electrospray; Gas phase chemistry; Theoretical calculations

Indexed keywords

BODY FLUIDS; ELECTROSPRAY IONIZATION; FUNGI; MASS SPECTROMETRY; PEPTIDES; TISSUE;

ANTIVIRAL PROPERTIES; ASPERGILLUS FUMIGATUS; DIKETOPIPERAZINES; GAS-PHASE CHEMISTRY; THEORETICAL CALCULATIONS;

AMINO ACIDS;

ION; PIPERAZINEDIONE;

ANTIMICROBIAL ACTIVITY; ASPERGILLUS FUMIGATUS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; PRIORITY JOURNAL; PROTON TRANSPORT; TANDEM MASS SPECTROMETRY; THERMODYNAMICS;

ASPERGILLUS FUMIGATUS; DIKETOPIPERAZINES; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

ASPERGILLUS FUMIGATUS;

EID: 35648948937     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1166     Document Type: Conference Paper

References (40)

1. Rudi A, Kashman Y, Benayahu Y, Schleyer M. Amino acid derivatives from the marine sponge Jaspis digonoxea. J. Nat. Prod. 1994; 57: 829.
2. Ström K, Sjögren J, Broberg A, Schnürer J. Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo(L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid. Appl. Environ. Microbiol. 2002; 68: 4322.
3. De Rosa S, Mitova M, Tommonaro G. Marine bacteria associated with sponge as source of cyclic peptides. Biomol. Eng. 2003; 20: 311.
4. Almassi F, Ghisalberti EL, Rowland CY. Rowland alkylcitrate-derived metabolites from Aspergillus niger. J. Nat. Prod. 1994; 57: 833.
5. Furtado NAJC, Pupo MT, Caravalho I, Campo VL, Duarte MCT, Bastos JK. Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain. J. Braz. Chem. Soc. 2005; 16: 1418.
6. Prasad C. Bioactive cyclic dipeptides. Peptides 1995; 16: 151.
7. Rhee KH. Cyclic dipeptides exhibit synergistic, broad spectrum antimicrobial effects and have anti-mutagenic properties. Int. J. Antimicrob. Agents 2004; 24: 423.
8. Brelles-Mariño G, Bedmar EJ. Detection, purification and characterization of quorum-sensing signal molecules in plant-associated bacteria. J. Bacteriol. 2001; 91: 197.
9. Corona MRC, Croft SL, Phillipson JD. Natural products as sources of antiprotozoal drugs. Curr. Opin. Anti-infect. Invest. Drugs 2000; 2: 47.
10. Yang SW, Chan IM, Ferracciano J, Loebenberg D, Chen G, Patel M, Gullo V, Pramanik B, Chu M. Structure elucidation of a new diketopiperazine Sch 725418 from Micromonospora sp. J. Antibiot. 2004; 57: 345.
11. Isaka M, Palasarn S, Rachtawee P, Vimuttipong S, Kongsaeree P. Unique diketopiperazine dimers from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449. Org. Lett. 2005; 7: 2257.
12. Elipe MVS. Advantages and disadvantages of nuclear magnetic resonance spectroscopy as a hyphenated technique. Anal. Chem. 2003; 497: 1.
13. Crotti AEM, Lopes JLC, Lopes NP. Triple quadrupole tandem mass spectrometry of sesquiterpene lactones: a study of goyazensolide and its congeners. J. Mass Spectrom. 2005; 40: 1030.
14. Pivatto M, Crotti AEM, Lopes NP, Castro-Gamboa I, Rezende A, Viegas C Jr, Young MCM, Furlan M, Bolzani VS. Electrospray ionization mass spectrometry screening of piperidine alkaloids from Senna spectabilis (Fabaceae) extracts: fast identification of new constituents and co-metabolites. J. Braz. Chem. Soc. 2005; 16: 1431.
15. +. J. Nat. Prod. 2005; 68: 385.
16. Crotti AEM, Vessecchi R, Lopes JLC, Lopes NP. Electrospray ionization mass spectrometry: chemical processes involved in the ion formation from low molecular weight organic compounds. Quim. Nova 2006; 2: 287.
17. Niessen WMA. Structure elucidation by LC-MS. Foreword. Analusis 2000; 28: 885.
18. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993; 98: 5648.
19. Petersson GA, Al-Laham MA. A complete basis set model chemistry. II. Open-shell systems and the total energies of the first-row atoms. J. Chem. Phys. 1991; 94: 6081.
20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Menucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komarini I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzales C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzales C, Head-Gordon M, Repogle ES, Pople JA. Gaussian 98 Revision A.7. Gaussian, Inc: Pittsburgh, PA, 1998.
21. Glendening ED, Weinhold F. Natural resonance theory: I. General formalism. J. Comput. Chem. 1998; 19: 593.
22. Crotti AEM, Fonseca T, Hong H, Staunton J, Galembeck SE, Lopes NP, Gates PJ. The fragmentation mechanism of five-membered lactones by electrospray ionization tandem mass spectrometry. Int. J. Mass Spectrom. 2004; 232: 271.
23. Vessecchi R, Nascimento PGBD, Lopes JNC, Lopes NP. Fragmentation studies of synthetic 2-acylamine-1,4-naphtoquinone by electrospray ionization mass spectrometry. J. Mass Spectrom. 2006; 41: 1219.
24. Bagno A, Bujnicki B, Bertrand S, Comuzzi C, Dorigo F, Janvier P, Scorrano G. Site of protonation of carboxylic and non-carboxylic amides in the gas phase and water. Chem. - Eur. J. 1999; 5: 523.
25. Contreras RR, Fuentealba P, Galván M, Pérez P. A direct evaluation of regional Fukui functions in molecules. Chem. Phys. Chem. 1999; 304: 405.
26. 14annulene complex and its protonated derivative. J. Phys. Chem. A 2004; 108: 7253.
27. Gabelica V, De Pauw E. Internal energy and fragmentation of íons produced in electrospray sources. Mass Spectrom. Rev. 2005; 24: 566.
28. Hammes GG. Principles of Chemical Kinetics. Academic Press: New York, 89.
29. Dongré AR, Jones JL, Somogyi A, Wysocki VH. Influence of peptide composition, gas-phase basicity and chemical modification on fragmentation efficiency: evidence for the mobile proton model. J. Am. Chem. Soc. 1996; 118: 8365.
30. Luo YR, Holmes JL. Homo- and heterolytic X-C bond energies. 1. Homolytic bond energies in commom unsaturated organic compounds. J. Phys. Chem. 1994; 98: 303.
31. Qin XZ. Tandem mass spectrum of a farnesyl transferase inhibitor-gas-phase rearrangements involving imidazole. J. Mass Spectrom. 2001; 36: 911.
32. Grob C. Mechanisms and stereochemistry of heterolytic fragmentation. Angew. Chem. Int. Ed. Engl. 1969; 8: 535.
33. Wharton OS, Hiegel GA. Fragmentation of 1,10-decalindiol tosylates. J. Org. Chem. 1965; 30: 3254.
34. Smith KM. Understanding Mass Spectra - a Basic Approach, 2nd edn. Wiley-Interscience: Hoboken, NJ, 2004; 111.
35. McLafferty FW, Turecek F. Interpretation of Mass Spectra, 4th edn. University Science Books: Mill Valey, CA, 1993; 117.
36. 2O and CO. Int. J. Mass Spectrom. 2006; 255-256: 265.
37. Radom L. Chemistry by computer: a theoretical approach to gas-phase ions. Org. Mass Spectrom. 1991; 26: 359.
38. Alcamí M, Mó O, Yáñez M. Computational chemistry: a useful (sometimes mandatory) toll in mass spectrometry studies. Mass Spectrom Rev. 2001; 20: 195.
39. McLafferty FW, Turecek F. Interpretation of Mass Spectra, 4th edn. University Science Books: Mill Valey, CA, 1993; 59.
40. March J. Advanced Organic Chemistry-Reactions, Mechanisms, and Structure, 4th edn. John Wiley and Sons: New York, 1992; 68.