Furanose C-C-linked γ -lactones: A combined ESI FTICR MS and semi-empirical calculations study

Journal of Mass Spectrometry

Volumn 45, Issue 10, 2010, Pages 1167-1178

  Madeira, Paulo J Amorim ^a   Xavier, Nuno M ^a   Rauter, Amélia P ^a   Florěncio, M Helena ^a  

^a UNIVERSITY OF LISBON   (Portugal)

Author keywords

FTICRMS; Ion structures; MOPAC; MS MS; Semi empirical calculations; SORI CAD fragmentation mechanisms; Sugars; , unsaturated lactones; hydroxy lactones

Indexed keywords

ELECTROSPRAY IONIZATION; IONS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PROTONATION;

FRAGMENTATION MECHANISM; FT-ICR MS; ION STRUCTURES; MOPAC; MS/MS; SEMI-EMPIRICAL CALCULATION;

SUGAR (SUCROSE);

4 (3 O ALLYL 1,2 O ISOPROISOPROPYLIDENE ALPHA DETRO XYLOFURANOS 4 YL) 4 HYDROXYDIHYDROFURAN 2(3H) ONE; 4 (3 O ALLYL 1,2 O ISOPROPYLIDENE ALPHA DEXTRO RIBOFURANOS 4 YL)FURAN 2(5H) ONE; 4 (3 O BENZYL 1,2 O ISOPROPYLIDENE ALPHA DEXTRO RIBOFURANOS 4 YL)FURAN 2(5H) ONE; 4 (3 O BENZYL 1,2 O ISOPROPYLIDENE ALPHA DEXTRO XYLOFURANOS 4 YL) 4 HYDROXYDIHYDROFURAN 2(3H) ONE; BUTENOLIDE; GAMMA LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; EMPIRICAL RESEARCH; FRAGMENTATION REACTION; PRIORITY JOURNAL;

EID: 78650829154     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1806     Document Type: Article

References (49)

1. N. M. Xavier, A. P. Rauter. Easy and Stereoselective Approach to α,β Unsaturated γ -Lactones Fused to Pyranoses from Furanose Scaffolds. Org. Lett. 2007, 9, 3339, DOI:10.1021/ol071351m.
2. N. M. Xavier, A. P. Rauter. Sugars containing α,β -unsaturated carbonyl systems: Synthesis and their usefulness as scaffolds in carbohydrate chemistry. Carbohydr. Res. 2008, 343, 1523, DOI: 10.1016/j.carres.2008.04.033.
3. A. P. Rauter, J. Figueiredo, M. Ismael, T. Canda, J. Font, M. Figueredo. Efficient synthesis of α,β-unsaturated γ -lactones linked to sugars. Tetrahedron: Asymmetry 2001, 12, 1131, DOI: 10.1016/S0957- 4166(01)00197-5.
4. D. Li, T. Zhu, H. Liu, Y. Fang, Q. Gu, W. Zhu. Four butenolides are novel cytotoxic compounds isolated from the marinederived bacterium, Streptoverticillium luteoverticillatum 11014. Arch. Pharmacal. Res. 2006, 29, 624, DOI: 10.1007/BF02968245.
5. S. Oh, I. H. Jeong, W.-S. Shin, Q. Wang, S. Lee. Synthesis and biological activity of (+)-hedychilactone A and its analogs from (+)-sclareolide. Bioorg. Med. Chem. Lett. 2006, 16, 1656, DOI: 10.1016/j.bmcl.2005.12.009. (Pubitemid 43197541)
6. H. I. El-Subbagh, S. M. Abu-Zaid, M. A. Mahran, F. A. Badria, A. M. Al- Obaid. Synthesis and Biological Evaluation of Certain α,β- Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents. J.Med. Chem. 2000, 43, 2915, DOI: 10.1021/jm000038m. (Pubitemid 30599649)
7. F. Cateni, J. Zilic, M. Zacchigna, P. Bonivento, F. Frausin, V. Scarcia. Synthesis and biological properties of new α-methylene-γ - butyrolactones and α,β-unsaturated δ-lactones. Eur. J. Med. Chem. 2006, 41, 192, DOI: 10.1016/j.ejmech.2005.10.009.
8. E. Paruch, J. Nawrot, C. Wawrzenczyk. Lactones: Part 11. Feedingdeterrent activity of some bi- and tricyclic terpenoid lactones. Pest Manage. Sci. 2001, 57, 776, DOI: 10.1002/ ps.353.
9. S. Ma, Z. Shi, Z. Yu. Synthesis of β-halobutenolides and their Pd(0)- catalyzed cross-coupling reactions with terminal alkynes and organozinc reagents. A general route to β-substituted butenolides and formal synthesis of cis-whisky lactone. Tetrahedron 1999, 55, 12137, DOI: 10.1016/S0040-4020(99) 00726-7. (Pubitemid 29453683)
10. J. Staunton, K. J. Weissman. Weissman. Polyketide biosynthesis: A millennium review. Nat. Prod. Rep. 2001, 18, 380, DOI: 10.1039/a909079g. (Pubitemid 32773840)
11. J. Justino, A. P. Rauter, T. Canda, R. Wilkins, E. Matthews. Sugar derivatives containing oxiranes and α,β-unsaturated γ -lactones as potential environmentally friendly insecticides. Pest Manage. Sci. 2005, 61, 985, DOI: 10.1002/ ps.1064.
12. P. Rüngeler, V. Castro, G. Mora, N. Gören, W. Vichnewski, H. L. Pahl, I. Merfort, T. J. Schmidt. Inhibition of transcription factor NF-κB by sesquiterpene lactones: A proposed molecular mechanism of action. Bioorg. Med. Chem. 1999, 7, 2343, DOI: 10.1016/S0968- 0896(99)00195-9.
13. M. L. C. Borsato, C. F. F. Grael, G. E. P. Souza, N. P. Lopes. Analgesic activity of the lignans from Lychnophora ericoides. Phytochemistry 2000, 55, 809, DOI: 10.1016/S0031-9422(00)00388-5.
14. L. S. Favier, A.O. M. María, G.H. Wendel, E. J. Borkowski, O. S. Giordano, L. Pelzer, C. E. Tonn. Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats. J. Ethnopharmacol. 2005, 100, 260, DOI: 10.1016/j.jep.2005.02.042. (Pubitemid 41206621)
15. N. M. Xavier, S. Silva, P. J. A. Madeira, M. H. Florêncio, F. V. M. Silva, J. Justino, J. Thiem, A. P. Rauter. Synthesis and Biological Evaluation of Sugars Containing α,β-Unsaturated γ -Lactones. Eur. J.Org.Chem. 2008, 2008, 6134, DOI: 10.1002/ejoc.200800763.
16. P. Kebarle, U. H. Verkerk. Electrospray: From ions in solution to ions in the gas phase, what we know now.Mass Spectrom. Rev. 2009, 28, 898, DOI: 10.1002/mas.20247.
17. T. R. Covey, B. A. Thomson, B. B. Schneider. Atmospheric pressure ion sources. Mass Spectrom. Rev. 2009, 28, 870, DOI: 10.1002/mas.20246.
18. N. B. Cech, C. G. Enke. Practical implications of some recent studies in electrospray ionization fundamentals. Mass Spectrom. Rev. 2001, 20, 362, DOI: 10.1002/mas.10008.
19. A. E.M. Crotti, T. Fonseca, H. Hong, J. Staunton, S. E. Galembeck, N. P. Lopes, P. J. Gates. The fragmentation mechanism of fivemembered lactones by electrospray ionisation tandem mass spectrometry. Int. J. Mass Spectrom. 2004, 232, 271, DOI: 10.1016/j.ijms.2004.02.009.
20. H. Desaire, J. A. Leary. Differentiation of Diastereomeric NAcetylhexosamine Monosaccharides Using Ion Trap Tandem Mass Spectrometry. Anal.Chem. 1999, 71, 1997, DOI: 10.1021/ac981052y. (Pubitemid 29233163)
21. S. G. Penn, M. T. Cancilla, C. B. Lebrilla. Collision-Induced Dissociation of Branched Oligosaccharide IonswithAnalysis and Calculation of Relative Dissociation Thresholds. Anal.Chem. 1996, 68, 2331, DOI: 10.1021/ac960155i.
22. J. Banoub, P. Thibault, P. Y. Gouéth, G. Ronco, P. Villa. Electrospray Tandem Mass Spectrometry of a Novel Series of Amphipathic Functionalized Ether-linked Diand Trisaccharides and Cyclic Oligosaccharides. J.Mass Spectrom. 1997, 32, 109, DOI: 10.1002/(SICI)1096- 9888(199701)32 : 1<109::AID-JMS459>3.0.CO;2-B
23. M. K. Young, N. Dinh, D. Williams. Analysis of N-acetylated hexosamine monosaccharides by ferrocenyl boronation and tandem electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2000, 14, 1462, DOI: 10.1002/1097- 0231(20000830)14 : 16<1462::AID-RCM48>3.0.CO;2-Y
24. W. Yin, Y. Ma, Y. Zhao. The fragmentation mechanism of β-(Nalkyl/arylamino)-α,β-unsaturated carboxylates under electrospray ionization conditions. Amino Acids 2006, 31, 333, DOI: 10.1007/s00726-006-0259-4. (Pubitemid 44537060)
25. P. J. A. Madeira, A. M. Rosa, N. M. Xavier, A. P. Rauter, M. H. Flor?encio. Electrospray Ionization Mass Spectrometry analysis of newly synthesised α,β-unsaturated ? -lactones fused to sugars. Rapid Commun. Mass Spectrom. 2010, 24, 1049, DOI: 10.1002/rcm.4490.
26. R. E. March, C. J. Stadey. A tandem mass spectrometric study of saccharides at high mass resolution. RapidCommun.Mass Spectrom. 2005, 19, 805, DOI: 10.1002/rcm.1860. (Pubitemid 40349421)
27. M. Beneito-Cambra, V. Bernabé-Zaf ón, J. M. Herrero-Martínez, G. Ramis-Ramos. Study of the Fragmentation of D-Glucose and Alkylmonoglycosides in the Presence of Sodium Ions in an Ion-Trap Mass Spectrometer. Anal. Lett. 2009, 42, 907. DOI: 10.1080/00032710902721956.
28. + adducts of dithioalkyl ketene acetals. RapidCommun.MassSpectrom.2001,15, 788, DOI: 10.1002/rcm.297. (Pubitemid 32479841)
29. K. P. Madhusudanan, B. Kumar, R. Pathak, C. S. Pant, A. K. Shaw. Tandem mass spectra of ammonium ion, metal ion and ligated metal ion adducts of acyclic sugar derivatives. Rapid Commun.Mass Spectrom. 2003, 17, 816, DOI: 10.1002/rcm.983. (Pubitemid 36433166)
30. K. P. Madhusudanan, B. Kumar, P. Tiwari, S. K. Madhusudan, A. K. Misra. Effect of metal cationization on the tandem mass spectra of glycosyl dithioacetals. J. Mass Spectrom. 2005, 40, 25, DOI: 10.1002/jms.767. (Pubitemid 40188977)
31. G. C. Justino, C. M. Borges, M. H. Flor êncio. Electrospray ionization tandem mass spectrometry fragmentation of protonated flavone and flavonol aglycones: A reexamination. Rapid Commun. Mass Spectrom. 2009, 23, 237, DOI: 10.1002/rcm.3869.
32. R. Franski, K. Eitner, M. Sikorska, I. Matlawska, M. Stobiecki. Electrospraymassspectrometricdecompositionofsomeglucuronic acid-containing flavonoid diglycosides. Phytochem. Anal. 2003, 14, 170, DOI: 10.1002/pca.703. (Pubitemid 36609244)
33. P. Przybylski, M. W3odarz, G. Schroeder, Pankiewicz Radosaw, B. Brzezinski, F. Bartl. ESI MS and PM5 semiempirical studies of gossypol schiff base with (R)-tetrahydrofurfurylamine complexes and monovalent cations. J. Mol. Struct. 2004, 693, 95, DOI: 10.1016/j.molstruc.2004.02.018. (Pubitemid 38510451)
34. 2+ cations studied by ESI-MS and PM5 methods. J. Mol. Struct. 2008, 886, 9, DOI: 10.1016/j.molstruc.2007.10.028. (Pubitemid 352043831)
35. K. Ishikawa, T. Nakamura, Y. Koga. Cross-checking of nanoelectrospray ionization mass spectrometry and computer simulation for the evaluation of the interaction strength of non-covalently bound enkephalins in solution. J. Mass Spectrom. 2001, 36, 937, DOI: 10.1002/jms.197. (Pubitemid 32827446)
36. M. A. Zayed, M. A. Fahmey, M. A. Hawash, A. A. El-Habeeb. Mass spectrometric investigation of buspirone drug in comparison with thermal analyses and MO-calculations. Spectrochim. Acta A 2007, 67, 522, DOI: 10.1016/j.saa.2006.08.021. (Pubitemid 46671528)
37. G. Khairallah, J. B. Peel. Cyano Adduct Anions of C70: Electrospray Mass Spectrometric Studies. J. Phys. Chem. A 1997, 101, 6770, DOI:10.1021/jp970635t.
38. J. Stewart. Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application to 70 elements. J. Mol. Model. 2007, 13, 1173, DOI: 10.1007/s00894-007- 0233-4. (Pubitemid 47629446)
39. J.J.P. MOPAC2009, Stewart Computational Chemistry: Colorado Springs, CO, USA, Stewart. 2009, http://openmopac.net. [Last accessed: 15 August 2010].
40. D. J. Harvey. Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. Mass Spectrom. Rev. 1999, 18, 349, DOI: 10.1002/(SICI)1098-2787(1999)18 : 6<349::AIDMAS1> 3.0.CO;2-H
41. T. Kazmaier, S. Roth, J. Zapp, M. Harding, R. Kuhn. Quantitative analysis of malto-oligosaccharides by MALDI-TOF mass spectrometry, capillary electrophoresis and anion exchange chromatography. Fresenius. J. Anal. Chem. 1998, 361, 473, DOI: 10.1007/s002160050928.
42. B. Domon, C. E. Costello. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J. 1988, 5, 397, DOI: 10.1007/BF01049915. (Pubitemid 19031141)
43. K. Kowski, W. Lüttke, P. Rademacher. Evidence for intramolecular OH. . .p hydrogen bonding in unsaturated alcohols from UV photoelectron spectroscopy. J. Mol. Struct. 2001, 567-568, 231, DOI: 10.1016/S0022-2860(01) 00556-7. (Pubitemid 32666522)
44. T. Solouki, B. B. Reinhold, C. E. Costello, M. O'Malley, S. Guan, A. G. Marshall. Electrospray Ionization and Matrix-Assisted Laser Desorption/ Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry of PermethylatedOligosaccharides. Anal.Chem. 1998, 70, 857, DOI: 10.1021/ac970562+. (Pubitemid 28141385)
45. S. A. McLuckey, D. E. Goeringer. Slow Heating Methods in Tandem Mass Spectrometry. J.Mass Spectrom. 1997, 32, 461.
46. E. G. Douglas, A. M. Scott. Evolution of ion internal energy during collisional excitation in the Paul ion trap: A stochastic approach. J. Chem. Phys. 1996, 104, 2214.
47. I. Starke, I. Schuster, F. Fülöp, E. Kleinpeter. Mass spectra of tetrahydroisoquinoline-fused 1,3,2-O,N,P- and 1,2,3-O,S,Nheterocycles: Influence of ring size and fusion, of present heteroatoms, substituent effects and of the stereochemistry on fragmentation. Rapid Commun.Mass Spectrom. 2008, 22, 1519, DOI: 10.1002/rcm.3543. (Pubitemid 351829693)
48. D. Lacey, X. K.Hu, A. V. Loboda, N. J.Mosey, R. H. Lipson. Aspirin revealed: A cationization strategy for detecting acetylsalicylic acid by MALDI mass spectrometry. Int. J. Mass Spectrom. 2007, 261, 192.
49. J. C. Ma,D. A. Dougherty.TheCation-π Interaction.Chem.Rev.1997, 97, 1303, DOI: 10.1021/cr9603744.