Linear ion trap MS n of enzymatically synthesized 13C-labeled fructans revealing differentiating fragmentation patterns of β (1-2) and β(1-6) fructans and providing a tool for oligosaccharide identification in complex mixtures

Analytical Chemistry

Volumn 84, Issue 3, 2012, Pages 1540-1548

  Harrison, Scott ^a,b   Xue, Hong ^a   Lane, Geoff ^a   Villas Boas, Silas ^b   Rasmussen, Susanne ^a  

^a AGRESEARCH GRASSLANDS   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL PRODUCTION; COMPLEX MIXTURE; FRAGMENTATION PATTERNS; FRUCTANS; GLYCOSIDIC BOND; HIGHER ORDER; HUMAN HEALTH; KESTOSE; LC-MS N; LINEAR ION TRAP; LOLIUM PERENNE; RING CLEAVAGE; STRESS PROTECTANTS;

CHROMATOGRAPHIC ANALYSIS; ISOMERS; OLIGOMERS; ORGANIC COMPOUNDS; PLANT EXTRACTS; SUGAR (SUCROSE);

POLYSACCHARIDES;

CARBON; FRUCTAN; GLYCOSYLTRANSFERASE; INULIN; INULOSUCRASE; OLIGOSACCHARIDE; RECOMBINANT PROTEIN;

ARTICLE; CHEMISTRY; ENZYMOLOGY; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOMERISM; LOLIUM; MASS SPECTROMETRY; METABOLISM;

CARBON ISOTOPES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUCTANS; HEXOSYLTRANSFERASES; HUMANS; INULIN; ISOMERISM; LOLIUM; MASS SPECTROMETRY; OLIGOSACCHARIDES; RECOMBINANT PROTEINS;

EID: 84856699962     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac202816y     Document Type: Article

References (28)

1. Hendry, G. A. F. Evolutionary origins and natural functions of fructans; a climatological, biogeographic and mechanistic appraisal New Phytol. 1993, 123 (1) 3-14 (Pubitemid 23390281)
2. Edwards, G. R.; Parsons, A. J.; Rasmussen, S.; Bryant, R. H. In High sugar ryegrasses for livestock systems in New Zealand; Proc. NZ Grasslands Assoc, 2007; pp 161-172.
3. Ritsema, T.; Smeekens, S. Fructans: beneficial for plants and humans Curr. Opin. Plant Biol. 2003, 6 (3) 223-230 (Pubitemid 36704507)
4. Andersen, M.; Kiel, P. Integrated utilisation of green biomass in the green biorefinery Ind. Crop Prod. 2000, 11 (2-3) 129-137 (Pubitemid 30172110)
5. Edelman, J.; Jefford, T. G. The Mechanisim of Fructosan Metabolism in Higher Plants as Exemplified in Helianthus tuberosus New Phytol. 1968, 67, 517-531
6. Pavis, N.; Chatterton, N. J.; Harrison, P. A.; Baumgartner, S.; Praznik, W.; Boucaud, J.; Prud'homme, M. P. Structure of fructans in roots and leaf tissues of Lolium perenne New Phytol. 2001, 150, 83-95 (Pubitemid 32265401)
7. Duchateau, N.; Bortlik, K.; Simmen, U.; Wiemken, A.; Bancal, P. Sucrose:Fructan 6-Fructosyltransferase, a Key Enzyme for Diverting Carbon from Sucrose to Fructan in Barley Leaves Plant Physiol. 1995, 107 (4) 1249-1255
8. Lasseur, B.; Lothier, J.; Djoumad, A.; De Coninck, B.; Smeekens, S.; Van Laere, A.; Morvan-Bertrand, A.; Van den Ende, W.; Prud'homme, M.-P. Molecular and functional characterization of a cDNA encoding fructan:fructan 6G-fructosyltransferase (6G-FFT)/fructan:fructan 1-fructosyltransferase (1-FFT) from perennial ryegrass (Lolium perenne L.) J. Exp. Bot. 2006, 57 (11) 2719-2734 (Pubitemid 44290303)
9. Lasseur, B.; Lothier, J.; Wiemken, A.; Van Laere, A.; Morvan-Bertrand, A.; Ende, W. V.; Prud'homme, M. P. Towards a better understanding of the generation of fructan structure diversity in plants: molecular and functional characterization of a sucrose: fructan 6-fructosyltransferase (6-SFT) cDNA from perennial ryegrass (Lolium perenne) J. Exp. Bot. 2011, 62 (6) 1871
10. Harrison, S. J.; Fraser, K.; Lane, G. A.; Villas-Boas, S.; Rasmussen, S. A reverse-phase liquid chromatography/mass spectrometry method for the analysis of high-molecular-weight fructooligosaccharides Anal. Biochem. 2009, 395 (1) 113-115
11. Jeffrey, G.; Park, Y. The crystal and molecular structure of 1-kestose Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1972, 28 (1) 257-267
12. Ferretti, V.; Bertolasi, V.; Gilli, G.; Accorsi, C. Structure of 6-kestose monohydrate, C18H31O16. H2O Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1984, 40 (3) 531-535
13. Sims, I. M.; Pollock, C. J.; Horgan, R. Structural analysis of oligomeric fructans from excised leaves of Lolium temulentum Phytochemistry 1992, 31, 2989-2992
14. Smouter, H.; Simpson, R. J. Occurrence of fructans in the Gramineae (Poaceae) New Phytol. 1989, 111, 359-368
15. Agrawal, P. K. NMR Spectroscopy in the Structural Elucidation of Oligosaccharides and Glycosides Phytochemistry 1992, 31, 3307-3330
16. Cairns, A. J. Fructan biosynthesis in transgenic plants J. Exp. Bot. 2003, 54 (382) 549-567 (Pubitemid 36122051)
17. Robinson, S.; Bergstrom, E.; Seymour, M.; Thomas-Oates, J. Screening of Underivatized Oligosaccharides Extracted from the Stems of Triticum aestivum Using Porous Graphitized Carbon Liquid Chromatography & Mass Spectrometry Anal. Chem. 2007, 79 (6) 2437-2445 (Pubitemid 46449025)
18. Koimur, M.; Lu, B.; Westerlund, D. High performance liquid chromatography of disaccharides on a porous graphitic carbon column applying post-column derivatization with benzamidine Chromatographia 1996, 43 (5) 254-260 (Pubitemid 26308705)
19. Tang, H.; Mechref, Y.; Novotny, M. V. Automated interpretation of MS/MS spectra of oligosaccharides Bioinformatics 2005, 21 (suppl-1) i431-439
20. Wuhrer, M.; Deelder, A. M.; van der Burgt, Y. E. M. Mass spectrometric glycan rearrangements Mass Spectrom. Rev. 2011, 30 (4) 664-680
21. Reinhold, V. N.; Reinhold, B. B.; Costello, C. E. Carbohydrate molecular weight profiling, sequence, linkage, and branching data: ES-MS and CID Anal. Chem. 1995, 67 (11) 1772-1784
22. Zaia, J. Mass spectrometry of oligosaccharides Mass Spectrom. Rev. 2004, 23 (3) 161-227
23. Stahl, M.; Von Brocke, A.; Bayer, E. Mass spectrometry of oligosaccharides. In Journal of Chromatography Library; Ziad El, R., Ed. Elsevier: 2002; Vol. 66, Chapter 27, pp 961-1042.
24. Harvey, D. J. Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update covering the period 2001-2002 Mass Spectrom. Rev. 2008, 27 (2) 125-201 (Pubitemid 351315898)
25. Domon, B.; Costello, C. E. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates Glycoconjugate J. 1988, 5 (4) 397-409 (Pubitemid 19031141)
26. St. John, J. A.; Sims, I. M.; Bonnett, G. D.; Simpson, R. J. Identification of products formed by a fructan: fructan fructosyltransferase activity from Lolium rigidum New Phytol. 1997, 135 (2) 249-257 (Pubitemid 28013919)
27. Allen, P. J.; Bacon, J. S. D. Oligosaccharides formed from sucrose by fructose-transferring enzymes of higher plants Biochem. J. 1956, 63 (2) 200-206
28. Fang, T. T.; Zirrolli, J.; Bendiak, B. Differentiation of the anomeric configuration and ring form of glucosyl-glycolaldehyde anions in the gas phase by mass spectrometry: isomeric discrimination between m/z 221 anions derived from disaccharides and chemical synthesis of m/z 221 standards Carbohydr. Res. 2007, 342 (2) 217-235 (Pubitemid 46073937)